Dimethoxybromoamphetamine (DOB), also known as brolamfetamine (INN) and bromo-DMA, is a psychedelic drug and substituted amphetamine of the phenethylamine class of compounds. DOB was first synthesized by Alexander Shulgin in 1967. Its synthesis and effects are documented in Shulgin's book PiHKAL: A Chemical Love Story.
2C-TFM is a psychedelic phenethylamine of the 2C family. It was first synthesized in the laboratory of David E. Nichols. It has also been called 2C-CF3, a name derived from the Para-trifluoromethyl group it contains.
2C-BFLY is a psychedelic phenethylamine and designer drug of the 2C family. It was first synthesized in 1996 by Aaron Monte, Professor of Chemistry at UW-La Crosse.
2,5-Dimethoxy-4-ethylamphetamine is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized by Alexander Shulgin, and was described in his book PiHKAL.
2C (2C-x) is a general name for the family of psychedelic phenethylamines containing methoxy groups on the 2 and 5 positions of a benzene ring. Most of these compounds also carry lipophilic substituents at the 4 position, usually resulting in more potent and more metabolically stable and longer acting compounds. Most of the currently known 2C compounds were first synthesized by Alexander Shulgin in the 1970s and 1980s and published in his book PiHKAL. Shulgin also coined the term 2C, being an acronym for the 2 carbon atoms between the benzene ring and the amino group.
Aleph is a psychedelic hallucinogenic drug and a substituted amphetamine of the phenethylamine class of compounds, which can be used as an entheogen. It was first synthesized by Alexander Shulgin, who named it after the first letter of the Hebrew alphabet. In his book PiHKAL, Shulgin lists the dosage range as 5–10 mg, with effects typically lasting for 6 to 8 hours.
2C-H (2,5-dimethoxyphenethylamine) is a lesser-known substituted phenethylamine of the 2C family.
Ariadne is a little-known psychoactive drug. It is a homologue of the psychedelics 2C-D and DOM. Ariadne was first synthesized by Alexander Shulgin. In his 1991 book PiHKAL, Shulgin reported testing Ariadne up to a dose of 32 mg, and reported that it produced "the alert of a psychedelic, with none of the rest of the package". Very little published data exists about the human pharmacology of Ariadne apart from Shulgin's limited testing; unpublished human trials reportedly observed some psychoactive effects, but no hallucinations.
2,5-Dimethoxy-4-butylamphetamine (DOBU) is a lesser-known psychedelic drug and a substituted amphetamine. DOBU was first synthesized by Alexander Shulgin. In his book PiHKAL (Phenethylamines i Have Known And Loved), only low dosages of 2–3 mg were tested, with the duration simply listed as "very long". DOBU produces paresthesia and difficulty sleeping, but with few other effects. Compared to shorter chain homologues such as DOM, DOET and DOPR which are all potent hallucinogens, DOBU has an even stronger 5-HT2 binding affinity but fails to substitute for hallucinogens in animals or produce hallucinogenic effects in humans, suggesting it has low efficacy and is thus an antagonist or weak partial agonist at the 5-HT2A receptor.
Dimethoxy-4-amylamphetamine (DOAM) is a lesser-known psychedelic drug and a substituted amphetamine. DOAM was first synthesized by Alexander Shulgin. In his book PiHKAL (Phenethylamines i Have Known And Loved), the minimum dosage is listed as 10 mg, and the duration is unknown. DOAM produces a bare threshold and tenseness. As the 4-alkyl chain length is increased from shorter homologues such as DOM, DOET and DOPR which are all potent hallucinogens, the 5-HT2 binding affinity increases, rising to a maximum with the 4-(n-hexyl) derivative before falling again with even longer chains, but compounds with chain length longer than n-propyl, or with other bulky groups such as isopropyl, t-butyl or γ-phenylpropyl at the 4- position, fail to substitute for hallucinogens in animals or produce hallucinogenic effects in humans, suggesting these have low efficacy and are thus antagonists or partial agonists at the 5-HT2A receptor.
2CBFly-NBOMe is a compound indirectly derived from the phenethylamine hallucinogen 2C-B, and related to benzodifurans like 2C-B-FLY and N-benzylphenethylamines like 25I-NBOMe. It was discovered in 2002, and further researched by Ralf Heim at the Free University of Berlin, and subsequently investigated in more detail by a team at Purdue University led by David E. Nichols. It acts as a potent partial agonist for the 5-HT2A serotonin receptor subtype.
2,5-Dimethoxy-4-fluoroamphetamine (DOF) is a psychedelic drug of the phenethylamine and amphetamine classes. Alexander Shulgin briefly describes DOF in his book PiHKAL:
Animal studies that have compared DOF to the highly potent DOI and DOB imply that the human activity will be some four to six times less than these two heavier halide analogues.
4-Substituted-2,5-dimethoxyamphetamines (DOx) is a chemical class of substituted amphetamine derivatives featuring methoxy groups at the 2- and 5- positions of the phenyl ring, and a substituent such as alkyl or halogen at the 4- position of the phenyl ring. Most compounds of this class are potent and long-lasting psychedelic drugs, and act as highly selective 5-HT2A, 5-HT2B, and 5-HT2C receptor partial agonists. A few bulkier derivatives such as DOAM have similarly high binding affinity for 5-HT2 receptors but instead act as antagonists, and so do not produce psychedelic effects though they retain amphetamine-like stimulant effects.
2CB-Ind is a conformationally-restricted derivative of the phenethylamine hallucinogen 2C-B, discovered in 1974 by Alexander Shulgin. It acts as a moderately potent and selective agonist for the 5-HT2A and 5-HT2C receptors, but unlike the corresponding benzocyclobutene derivative TCB-2 which is considerably more potent than the parent compound 2C-B, 2CB-Ind is several times weaker, with racemic 2CB-Ind having a Ki of 47nM at the human 5-HT2A receptor, only slightly more potent than the mescaline analogue (R)-jimscaline.
2C-T-16 is a lesser-known psychedelic drug. It was originally named by Alexander Shulgin as described in his book PiHKAL, however while Shulgin began synthesis of this compound he only got as far as the nitrostyrene intermediate, and did not complete the final synthetic step. Synthesis of 2C-T-16 was finally achieved by Daniel Trachsel some years later, and it was subsequently reported as showing similar psychedelic activity to related compounds, with a dose range of 10–25 mg and a duration of 4–6 hours, making it around the same potency as the better-known saturated analogue 2C-T-7, but with a significantly shorter duration of action. Binding studies in vitro showed 2C-T-16 to have a binding affinity of 44 nM at 5-HT2A and 15 nM at 5-HT2C. 2C-T-16 and related derivatives are potent partial agonists of the 5-HT1A, 5-HT2A, 5-HT2B and 5-HT2C receptors and induce a head-twitch response in mice.
25B-NBOH is a derivative of the phenethylamine derived hallucinogen 2C-B which has been sold as a designer drug. It acts as a potent serotonin receptor agonist with similar affinity to the better-known compound 25B-NBOMe at 5-HT2A and 5-HT2C receptors with pKis values of 8.3 and 9.4, respectively.
2,5-Dimethoxy-4-isopropylamphetamine is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized by Alexander Shulgin, and was described in his book PiHKAL. Shulgin described DOiPR as being at least an order of magnitude weaker than DOPr, with doses of 20–30 mg required to produce valid changes in mental state. Very little data exists about the pharmacological properties, metabolism, and toxicity of DOiPR.
2C-B-BUTTERFLY is a conformationally-restricted derivative of the phenethylamine hallucinogen 2C-B, which was discovered in 1999 by Michael S. Whiteside and Aaron Monte. It is a ring-expanded homologue of the better known compound 2C-B-FLY, and has similar properties as an agonist for serotonin receptors, but with more selectivity for 5-HT2C over 5-HT2A.
25B-NBF is a derivative of the phenethylamine hallucinogen 2C-B, which acts as a highly potent partial agonist for the human 5-HT2A receptor.
CYB210010 (2C-T-TFM) is a lesser-known psychedelic drug related to compounds such as 2C-T and 2C-T-21. Alexander Shulgin attempted to synthesise this compound in the 1990s, and mentions it in his book PiHKAL under the entry for 2C-T-21, but was unsuccessful in producing a key intermediate and never assigned it a 2C-T number. This compound was ultimately first synthesised by Geoffrey Varty and colleagues at Irish biopharmaceutical company Cybin in 2023. It has a Ki of 0.35 nM at 5-HT2A, and an EC50 of 4.1 nM at 5-HT2A and 7.3 nM at 5-HT2C, compared to 88 nM at 5-HT2B. It is a potent, selective, long acting and orally active agonist for the 5-HT2A and 5-HT2C receptors and produces psychedelic-like responding in several different animal species. It is not known to have been tested in humans.
