A hallucinogen is a psychoactive agent which can cause hallucinations, perceptual anomalies, other substantial subjective changes in thoughts and consciousness. The common types of hallucinogens are psychedelics and deliriants. Although hallucinations are a common symptom of amphetamine psychosis, amphetamines are not considered hallucinogens, as they are not a primary effect of the drugs themselves. While hallucinations can occur when abusing stimulants, the nature of stimulant psychosis is not unlike delirium. A debate persists on criteria which would differentiate a substance which is'psychedelic' from one'hallucinogenic'. Sir Thomas Browne in 1646 coined the term'hallucination' from the Latin word "alucinari" meaning "to wander in the mind"; the term'psychedelic' is derived from the Ancient Greek words psychē and dēloun, or "mind-revealing".'A hallucinogen' and'a psychedelic' may refer to the same substance.'Hallucinations' and'psychedelia' may both refer to the same aspects of subjective experience in a given instance.
The term psychedelia carries an added reference to psychedelic substance culture, and'psychedelics' are considered by many to be the'traditional' or'classical hallucinogens' including DMT, Psilocybin, LSD.'A hallucinogen' in this sense broadly refers to any substance which causes changes in perception or hallucinations, while psychedelics carry a positive connotation of general perceptual enhancement. In contrast to Hollister's original criteria, adverse effects may predominate with some hallucinogens with this application of the term; the word psychedelic was coined to express the idea of a drug that makes manifest a hidden but real aspect of the mind. It is applied to any drug with perception-altering effects such as LSD and other ergotamine derivatives, DMT and other tryptamines including the alkaloids of Psilocybe spp. mescaline and other phenethylamines. The term "psychedelic" is applied somewhat interchangeably with "psychotomimetic" and "hallucinogen", The classical hallucinogens are considered to be the representative psychedelics and LSD is considered the prototypical psychedelic.
In order to refer to the LSD-like psychedelics, scientific authors have used the term "classical hallucinogen" in the sense defined by Glennon: "The classical hallucinogens are agents that meet Hollister's original definition, but are agents that: bind at 5-HT2 serotonin receptors, are recognized by animals trained to discriminate 1--2-aminopropane from vehicle. Otherwise, when the term "psychedelic" is used to refer only to the LSD-like psychedelics, authors explicitly point that they intend "psychedelic" to be understood according to this more restrictive interpretation. One explanatory model for the experiences provoked by psychedelics is the "reducing valve" concept, first articulated in Aldous Huxley's book The Doors of Perception. In this view, the drugs disable the brain's "filtering" ability to selectively prevent certain perceptions, emotions and thoughts from reaching the conscious mind; this effect has been described as mind expanding, or consciousness expanding, for the drug "expands" the realm of experience available to conscious awareness.
While possessing a unique mechanism of action, cannabis or marijuana has been regarded alongside the classic psychedelics. A designer drug is a structural or functional analog of a controlled substance, designed to mimic the pharmacological effects of the original drug while at the same time avoid being classified as illegal and/or avoid detection in standard drug tests. Many designer drugs and research chemicals are hallucinogenic in nature, such as those in the 2C and 25-NB families. Dissociatives produce analgesia and catalepsy at anesthetic doses, they produce a sense of detachment from the surrounding environment, hence "the state has been designated as dissociative anesthesia since the patient seems disassociated from his environment." Dissociative symptoms include the disruption or compartmentalization of "...the integrated functions of consciousness, identity or perception."p. 523 Dissociation of sensory input can cause derealization, the perception of the outside world as being dream-like or unreal.
Other dissociative experiences include depersonalization, which includes feeling detached from one's body. Simeon offered "...common descriptions of depersonalisation experiences: watching oneself from a distance. However, dissociation is remarkably administered by salvinorin A's potent κ-opioid receptor agonism, though sometimes described as an atypical psychedelic; some dissociatives can have CNS depressant effects, thereby carrying similar risks as opioids, which can slow breathing or heart rate to levels resulting in death (w
TIHKAL: The Continuation is a 1997 book written by Alexander Shulgin and Ann Shulgin about a family of psychoactive drugs known as tryptamines. A sequel to PIHKAL: A Chemical Love Story, TIHKAL is an acronym that stands for "Tryptamines I Have Known and Loved". TIHKAL, much like its predecessor PIHKAL, is divided into two parts; the first part, for which all rights are reserved, begins with a fictionalized autobiography, picking up where the similar section of PIHKAL left off. The second part of TIHKAL, which may be conditionally distributed for non-commercial reproduction, is a detailed synthesis manual for 55 psychedelic compounds, including their chemical structures, dosage recommendations, qualitative comments. Shulgin has made the second part available on Erowid.org while the first part is available only in the printed text. Like PIHKAL, the Shulgins were motivated to release the synthesis information as a way to protect the public's access to information about psychedelic compounds, a goal Alexander Shulgin has noted many times.
Following a raid of his laboratory in 1994 by the United States DEA, Richard Meyer, spokesman for DEA's San Francisco Field Division, stated that "It is our opinion that those books are pretty much cookbooks on how to make illegal drugs. Agents tell me that in clandestine labs that they have raided, they have found copies of those books." PiHKAL, the 1991 book by the same authors, on phenethylamines. Erowid Online Books: TIHKAL: The Continuation by Alexander & Ann Shulgin "Shulgin in Spanish" Project - Information on the first complete translation of PIHKAL and TIHKAL into Spanish TIHKAL • Info: A visual index and map of TIHKAL, including the formatted text of Book II. Includes over 300 corrections to the original HTML version
Nicholas Sand was a cult figure known in the psychedelic community for his work as a clandestine chemist from 1966-1996 for The Brotherhood of Eternal Love. Sand was part of the League for Spiritual Discovery at the Millbrook estate in New York, has been credited as the "first underground chemist on record to have synthesized DMT" and is known for manufacturing large amounts of LSD. Sand was born in Brooklyn, New York City on May 10, 1941, his father Clarence Hiskey, was a researcher in the Manhattan Project's Metallurgical Laboratory who attempted to spy for the Soviet Union. After his parents divorced, Sand took his mother's maiden name. Sand graduated from Erasmus Hall High School in 1959 and spent a year working on a kibbutz in Israel, he graduated from Brooklyn College with a degree in anthropology and sociology in 1966. Sand became interested in the teachings of George Gurdjieff, the study of different cultures, various Eastern philosophers. In 1961, he had his first mescaline experience.
Shortly after graduating from college, Sand followed Alpert to Millbrook. During this time Sand began synthesizing DMT in his bathtub, he is credited with being the first to discover that it was active when volatized. Sand started a perfume company as a front for the production of mescaline and DMT. Nick Sand and David L. Mantell were arrested on April 1, 1967 when their truck failed to stop at the Dinosaur, Colorado Port of Entry; the truck was searched and federal agents found 313,000 doses of LSD and a laboratory-on-wheels. In 1967 Sand was introduced to fellow chemist Tim Scully, who trained under Owsley Stanley until Stanley's legal troubles in December 1967. In December 1968 Sand purchased a secluded farmhouse in Windsor, California, at that time a small town in rural Sonoma County. There he and Scully set up a large LSD lab. Here they produced over 3.6 million tablets of LSD, distributed under the name "orange sunshine". A joint state and local strike force called "Operation BEL" was assembled in early 1972.
On August 3, 1972 the Orange County, California Grand Jury returned an indictment against 29 alleged members of The Brotherhood of Eternal Love, including Nick Sand. The investigation continued and on December 6, 1972 the Orange County, California Grand Jury returned another indictment, this time aimed against the Brotherhood of Eternal Love's "orange sunshine" LSD system. On January 19, 1973 "Leland H. Jordan" and Judy Neal Shaughnessy were arrested on drug charges by Kirkwood, MO police, shortly after they arrived from San Francisco, their residence at 425 North Highway 21 in Fenton, MO, an elaborate hilltop home on 18 acres of land, had been found to contain hundreds of gallons of chemicals and elaborate laboratory equipment. On April 25, 1973, Nicholas Sand, Tim Scully, Michael Randall, four other major figures in the LSD operation were indicted by a Federal grand jury in San Francisco, California. On January 30, 1974 Nicholas Sand and Tim Scully were found guilty due to the testimony of Billy Hitchcock and other "snitches".
On March 8, 1974 Sand was sentenced to 15 years in a federal penitentiary. The defense presented at his trial claimed that the defendants had made ALD-52 instead of LSD-25. Sand's attorney appealed his conviction, based on four technical legal issues: pre-indictment delay, refusal to suppress bank records, lack of a taint hearing and use of Swiss Bank Records; the appeal was denied by the 9th Circuit Court of Appeals on September 13, 1976 and rehearing was denied October 8, 1976. LSD chemist William Leonard Pickard contributed to Sand's legal defense fund. Nicholas Sand fled to Canada in 1976. LSD historian Mark McCloud reports that Sand traveled to the ashram of so-called "sex guru" Rajneesh in west India. Sand returned to North America, again producing large quantities of LSD. Sand was arrested for drug manufacturing in 1990 in British Columbia, but as he was living under an alias, police did not determine his identity and Sand fled while on bail. Sand was arrested again in 1996 in Canada. Refusing to cooperate with the police, it took forensic investigators two months to determine Sand's real identity.
Police found 43 grams of crystalline LSD at Sand's lab 430,000 doses of LSD. The bust uncovered large quantities of DMT, 2C-B, MDMA, $500,000 worth of cash and gold. LSD historian Jesse Jarnow suggests that Sand's arrest was a factor leading to the turn-of-the-century decline in availability of LSD in the United States. Sand died of a heart attack in his sleep at his home in Lagunitas, California on April 24, 2017 at the age of 75. Tim Scully Owsley Stanley William Leonard Pickard Casey William Hardison History of lysergic acid diethylamide Psychonautics Counterculture of the 1960s The Sunshine Makers Erowid Character Vaults: Nick Sand Erowid Character Vaults: Nick Sand Extended Biography Audio: Nick Sand at Mind States II in 2001 Audio: Nick Sand giving his 2006 Palenque Norte lecture at Burning Man
Hydrolysis is a term used for both an electro-chemical process and a biological one. The hydrolysis of water is the separation of water molecules into hydrogen and oxygen atoms using electricity. Biological hydrolysis is the cleavage of biomolecules where a water molecule is consumed to effect the separation of a larger molecule into component parts; when a carbohydrate is broken into its component sugar molecules by hydrolysis, this is termed saccharification. Hydrolysis or saccharification is a step in the degradation of a substance. Hydrolysis can be the reverse of a condensation reaction in which two molecules join together into a larger one and eject a water molecule, thus hydrolysis adds water to break down, whereas condensation builds up by removing water and any other solvents. Some hydration reactions are hydrolysis. Hydrolysis is a chemical process in which a molecule of water is added to a substance. Sometimes this addition causes both water molecule to split into two parts. In such reactions, one fragment of the target molecule gains a hydrogen ion.
It breaks a chemical bond in the compound. A common kind of hydrolysis occurs when a salt of weak base is dissolved in water. Water spontaneously ionizes into hydroxide anions and hydronium cations; the salt dissociates into its constituent anions and cations. For example, sodium acetate dissociates in water into acetate ions. Sodium ions react little with the hydroxide ions whereas the acetate ions combine with hydronium ions to produce acetic acid. In this case the net result is a relative excess of hydroxide ions. Strong acids undergo hydrolysis. For example, dissolving sulfuric acid in water is accompanied by hydrolysis to give hydronium and bisulfate, the sulfuric acid's conjugate base. For a more technical discussion of what occurs during such a hydrolysis, see Brønsted–Lowry acid–base theory. Acid–base-catalysed hydrolyses are common, their hydrolysis occurs when the nucleophile attacks the carbon of the carbonyl group of the ester or amide. In an aqueous base, hydroxyl ions are better nucleophiles than polar molecules such as water.
In acids, the carbonyl group becomes protonated, this leads to a much easier nucleophilic attack. The products for both hydrolyses are compounds with carboxylic acid groups; the oldest commercially practiced example of ester hydrolysis is saponification. It is the hydrolysis of a triglyceride with an aqueous base such as sodium hydroxide. During the process, glycerol is formed, the fatty acids react with the base, converting them to salts; these salts are called soaps used in households. In addition, in living systems, most biochemical reactions take place during the catalysis of enzymes; the catalytic action of enzymes allows the hydrolysis of proteins, fats and carbohydrates. As an example, one may consider proteases, they catalyse the hydrolysis of interior peptide bonds in peptide chains, as opposed to exopeptidases. However, proteases do not catalyse the hydrolysis of all kinds of proteins, their action is stereo-selective: Only proteins with a certain tertiary structure are targeted as some kind of orienting force is needed to place the amide group in the proper position for catalysis.
The necessary contacts between an enzyme and its substrates are created because the enzyme folds in such a way as to form a crevice into which the substrate fits. Therefore, proteins that do not fit into the crevice will not undergo hydrolysis; this specificity preserves the integrity of other proteins such as hormones, therefore the biological system continues to function normally. Upon hydrolysis, an amide converts into an amine or ammonia. One of the two oxygen groups on the carboxylic acid are derived from a water molecule and the amine gains the hydrogen ion; the hydrolysis of peptides gives amino acids. Many polyamide polymers such as nylon 6,6 hydrolyse in the presence of strong acids; the process leads to depolymerization. For this reason nylon products fail by fracturing. Polyesters are susceptible to similar polymer degradation reactions; the problem is known as environmental stress cracking. Hydrolysis is related to energy storage. All living cells require a continual supply of energy for two main purposes: the biosynthesis of micro and macromolecules, the active transport of ions and molecules across cell membranes.
The energy derived from the oxidation of nutrients is not used directly but, by means of a complex and long sequence of reactions, it is channelled into a special energy-storage molecule, adenosine triphosphate. The ATP molecule contains pyrophosphate linkages. ATP can undergo hydrolysis in two ways: the removal of terminal phosphate to form adenosine diphosphate and inorganic phosphate, or the removal of a terminal diphosphate to yield adenosine monophosphate and pyrophosphate; the latter undergoes further cleavage in
2C-B-FLY is a psychedelic phenethylamine of the 2C family. It was first synthesized in 1996 by Aaron P. Monte. 2C-B-FLY is 8-bromo-2,3,6,7-benzo-dihydro-difuran-ethylamine. The full name of the chemical is 2-ethanamine, it has been subject to little formal study, but its appearance as a designer drug has led the DEA to release analytical results for 2C-B-FLY and several related compounds. In theory, dihydrodifuran analogues of any of the 2Cx / DOx family of drugs could be made, would be expected to show similar activity to the parent compound. So in the same way that 2C-B-FLY is the dihydrodifuran analogue of 2C-B, the 8-iodo equivalent 2C-I-FLY would be the dihydrodifuran analogue of 2C-I, the 8-methyl equivalent 2C-D-FLY would be the dihydrodifuran analogue of 2C-D. Other related compounds can be produced, where the alpha carbon of the ethylamine chain is methylated, the amphetamine derivative DOB-FLY can be made, this compound being the dihydrodifuran analogue of DOB, or conversely can be viewed as the saturated derivative of Bromo-DragonFLY.
Where only one methoxy group of a 2Cx drug is cyclised into a dihydrofuran ring, the resulting compound is known as a "hemifly", when an unsaturated furan ring is used, the compound is known as a "hemi-dragonfly". The larger saturated hexahydrobenzodipyran ring derivatives have been referred to as "butterfly" compounds; the 8-bromo group can be replaced by other groups to give compounds such as TFMFly. A large number of symmetrical and unsymmetrical derivatives can be produced by using different combinations of ring systems; because the 2- and 5- positions are not equivalent, all unsymmetrical combinations have two possible positional isomers, with different potencies at the various 5-HT2 subtypes. Isomeric "Ψ"-derivatives with the oxygens positioned at the 2,6- positions, mescaline analogues with the oxygens at 3,5- have been made, but both are less potent than the corresponding 2,5- isomers; the symmetrical aromatic benzodifuran derivatives tend to have the highest binding affinity at 5-HT2A, but the saturated benzodifuran derivatives have higher efficacy, while the saturated benzodipyran derivatives are more selective for 5-HT2C.
A large number of possible combinations have been synthesised and tested for activity, but these represent only a fraction of the many variations that could be produced. Alexander Shulgin lists a dosage of 2C-B-FLY at 10 mg orally; the toxicity of 2C-B-FLY in humans is unknown. Two deaths occurred in October 2009, in Denmark and the United States, after ingestion of a substance, sold as 2C-B-FLY a small-time RC shop, but in fact consisted of Bromo-DragonFLY contaminated with a small amount of unidentified impurities; as of October 31, 2016. Http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php 2C-B-FLY is unscheduled and uncontrolled in the United States. However, it may fall under the scope of the Federal Analog Act if it is intended for human consumption given its similarity to 2C-B; the hallucinogenic effect of 2C-B-FLY is mediated by its partial agonistic activity at the 5-HT2A serotonin receptor, but has a high binding affinity for the 5-HT1D, 5-HT1E, 5-HT1A, 5-HT2B and 5-HT2C receptors.
2C-B-FLY Entry at Erowid 2C-B-FLY Entry at Isomerdesign
Alexander Theodore Shulgin was an American medicinal chemist, organic chemist, psychopharmacologist, author. He is credited with introducing MDMA to psychologists in the late 1970s for psychopharmaceutical use and for the discovery and personal bioassay of over 230 psychoactive compounds for their psychedelic and entactogenic potential. In 1991 and 1997, he and his wife Ann Shulgin authored the books PIHKAL and TIHKAL, which extensively described their work and personal experiences with these two classes of psychoactive drugs. Shulgin performed seminal work into the descriptive synthesis of many of these compounds; some of Shulgin's noteworthy discoveries include compounds of the 2C* family and compounds of the DOx family. Due in part to Shulgin's extensive work in the field of psychedelic research and the rational drug design of psychedelic drugs, he has since been dubbed the "godfather of psychedelics". Shulgin was born in California, to Theodore Stevens Shulgin and Henrietta D. Shulgin, his father was born in Russia.
Both Theodore and Henrietta were public school teachers in Alameda County. Shulgin began studying organic chemistry as a Harvard University scholarship student at the age of 16. In 1943 he dropped out of school to join the U. S. Navy. While serving on USS Pope in the Navy during World War II, Shulgin was given a glass of orange juice by a nurse prior to surgery for a thumb infection. Shulgin drank the juice and, assuming that the powder at the bottom of the glass was a sedative, fell asleep rapidly. Upon waking he learned; the experience made him aware of the influence of placebos over the human mind. After serving in the Navy, Shulgin returned to Berkeley, in 1954 earned his PhD in biochemistry from the University of California, Berkeley. Through the late 1950s Shulgin completed post-doctoral work in the fields of psychiatry and pharmacology at University of California, San Francisco. After working at Bio-Rad Laboratories as a research director for a brief period, he began work at Dow Chemical Company as a senior research chemist.
At this time he had a series of psychedelic experiences that helped to shape his further goals and research, the first of, brought on by mescaline. "I first explored mescaline in the late'50s... Three-hundred-fifty to 400 milligrams. I learned there was a great deal inside me."Shulgin reported personal revelations that "had been brought about by a fraction of a gram of a white solid, but that in no way whatsoever could it be argued that these memories had been contained within the white solid... I understood that our entire universe is contained in the spirit. We may choose not to find access to it, we may deny its existence, but it is indeed there inside us, there are chemicals that can catalyze its availability." Shulgin's professional activities continued to lean in the direction of psychopharmacology, furthered by his personal experiences with psychedelics. But during this period he was unable to do much independent research, his opportunity for further research came in 1961 after his development of Zectran, the first biodegradable pesticide, a profitable product.
In his book PIHKAL, Shulgin limits his pesticide days at Dow Chemical to one sentence in 978 pages. Dow Chemical Company, in return for Zectran's valuable patent, gave Shulgin great freedom. During this time, he created and patented drugs when Dow asked, published findings on other drugs in journals such as Nature and the Journal of Organic Chemistry. Dow Chemical requested that he no longer use their name on his publications. In late 1966, Shulgin left Dow, he first spent two years studying neurology at the University of California, San Francisco School of Medicine, leaving to work on a consulting project. He set up a home-based lab on his property, known as "the Farm", became a private consultant, he taught classes in the local universities and at the San Francisco General Hospital. Through his friend Bob Sager, head of the U. S. DEA's Western Laboratories, Shulgin formed a relationship with the DEA and began holding pharmacology seminars for the agents, supplying the DEA with samples of various compounds, serving as an expert witness in court.
In 1988, he authored a then-definitive law enforcement reference book on controlled substances, received several awards from the DEA. In order to work with scheduled psychoactive chemicals, Shulgin obtained a DEA Schedule I license for an analytical laboratory, which allowed him to synthesize and possess any otherwise illicit drug. Shulgin set up a chemical synthesis laboratory in a small building behind his house, which gave him a great deal of career autonomy. Shulgin used this freedom to synthesize and test the effects of psychoactive drugs. In 1976, Shulgin was introduced to MDMA by a student in the medicinal chemistry group he advised at San Francisco State University. MDMA had been synthesized in 1912 by Merck and patented in 1913 as an intermediate of another synthesis in order to block competitors, but was never explored in its own right. Shulgin went on to develop a new synthesis method, in 1976, introduced the chemical to Leo Zeff, a psychologist from Oakland, California. Zeff used the substance in his practice in small doses as an aid to talk therapy.
Zeff introduced the substance to hundreds of psychologists and lay therapists around the nation, including Ann, whom Alexander Shulgin met in 1979, married in 1981. It was her fo
Simplified molecular-input line-entry system
The simplified molecular-input line-entry system is a specification in the form of a line notation for describing the structure of chemical species using short ASCII strings. SMILES strings can be imported by most molecule editors for conversion back into two-dimensional drawings or three-dimensional models of the molecules; the original SMILES specification was initiated in the 1980s. It has since been extended. In 2007, an open standard called. Other linear notations include the Wiswesser line notation, ROSDAL, SYBYL Line Notation; the original SMILES specification was initiated by David Weininger at the USEPA Mid-Continent Ecology Division Laboratory in Duluth in the 1980s. Acknowledged for their parts in the early development were "Gilman Veith and Rose Russo and Albert Leo and Corwin Hansch for supporting the work, Arthur Weininger and Jeremy Scofield for assistance in programming the system." The Environmental Protection Agency funded the initial project to develop SMILES. It has since been modified and extended by others, most notably by Daylight Chemical Information Systems.
In 2007, an open standard called "OpenSMILES" was developed by the Blue Obelisk open-source chemistry community. Other'linear' notations include the Wiswesser Line Notation, ROSDAL and SLN. In July 2006, the IUPAC introduced the InChI as a standard for formula representation. SMILES is considered to have the advantage of being more human-readable than InChI; the term SMILES refers to a line notation for encoding molecular structures and specific instances should be called SMILES strings. However, the term SMILES is commonly used to refer to both a single SMILES string and a number of SMILES strings; the terms "canonical" and "isomeric" can lead to some confusion when applied to SMILES. The terms are not mutually exclusive. A number of valid SMILES strings can be written for a molecule. For example, CCO, OCC and CC all specify the structure of ethanol. Algorithms have been developed to generate the same SMILES string for a given molecule; this SMILES is unique for each structure, although dependent on the canonicalization algorithm used to generate it, is termed the canonical SMILES.
These algorithms first convert the SMILES to an internal representation of the molecular structure. Various algorithms for generating canonical SMILES have been developed and include those by Daylight Chemical Information Systems, OpenEye Scientific Software, MEDIT, Chemical Computing Group, MolSoft LLC, the Chemistry Development Kit. A common application of canonical SMILES is indexing and ensuring uniqueness of molecules in a database; the original paper that described the CANGEN algorithm claimed to generate unique SMILES strings for graphs representing molecules, but the algorithm fails for a number of simple cases and cannot be considered a correct method for representing a graph canonically. There is no systematic comparison across commercial software to test if such flaws exist in those packages. SMILES notation allows the specification of configuration at tetrahedral centers, double bond geometry; these are structural features that cannot be specified by connectivity alone and SMILES which encode this information are termed isomeric SMILES.
A notable feature of these rules is. The term isomeric SMILES is applied to SMILES in which isotopes are specified. In terms of a graph-based computational procedure, SMILES is a string obtained by printing the symbol nodes encountered in a depth-first tree traversal of a chemical graph; the chemical graph is first trimmed to remove hydrogen atoms and cycles are broken to turn it into a spanning tree. Where cycles have been broken, numeric suffix labels are included to indicate the connected nodes. Parentheses are used to indicate points of branching on the tree; the resultant SMILES form depends on the choices: of the bonds chosen to break cycles, of the starting atom used for the depth-first traversal, of the order in which branches are listed when encountered. Atoms are represented by the standard abbreviation of the chemical elements, in square brackets, such as for gold. Brackets may be omitted in the common case of atoms which: are in the "organic subset" of B, C, N, O, P, S, F, Cl, Br, or I, have no formal charge, have the number of hydrogens attached implied by the SMILES valence model, are the normal isotopes, are not chiral centers.
All other elements must be enclosed in brackets, have charges and hydrogens shown explicitly. For instance, the SMILES for water may be written as either O or. Hydrogen may be written as a separate atom; when brackets are used, the symbol H is added if the atom in brackets is bonded to one or more hydrogen, followed by the number of hydrogen atoms if greater than 1 by the sign + for a positive charge or by - for a negative charge. For example, for ammonium. If there is more than one charge, it is written as digit.