2C (psychedelics)

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General structure of a 2C compound 2C-general.png
General structure of a 2C compound

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. [1] [2] [3] 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. [4]

Contents

Most of the currently known 2C compounds were first synthesized by Alexander Shulgin in the 1970s and 1980s and published in his book PiHKAL (Phenethylamines i Have Known And Loved). [3] Shulgin also coined the term 2C, being an acronym for the 2 carbon atoms between the benzene ring and the amino group. [5] [1] [3] 2C-B is the most popular of the 2C drugs. [3]

Pharmacology

Pharmacodynamics

The 2C drugs act as agonists of the serotonin 5-HT2 receptors, including of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors. [6] [7] [8] [9] Most of the 2C drugs have much lower affinity for the serotonin 5-HT1A receptor than for the serotonin 5-HT2A receptor. [6] [7] [8] Their psychedelic effects are thought to be mediated specifically by activation of the serotonin 5-HT2A receptor. [7] [9]

Unlike many other phenethylamines, 2C drugs, including 2C-C, 2C-D, 2C-E, 2C-I, and 2C-T-2 among others, are inactive as monoamine releasing agents and reuptake inhibitors. [10] [7] [6] [9]

Most of the 2C drugs are agonists of the rat and mouse trace amine-associated receptor 1 (TAAR1). [11] [12] [6] However, most are inactive as agonists of the human TAAR1. [11] [12] [6]

Pharmacokinetics

The 2C drugs are orally active and most have doses in the range of 10 to 60 mg and durations in the range of 4 to 12 hours. [1] They are metabolized by O-demethylation and deamination (by monoamine oxidases). [1]

History

2,4,5-Trimethoxyphenethylamine (2,4,5-TMPEA; 2C-O or "2C-MeO") was first synthesized by Jansen and was found to produce psychedelic effects similar to those of mescaline (3,4,5-trimethoxyphenethylamine). [13] [14] He published his findings in 1931. [13] [14] However, subsequent studies in the 1960s and 1970s suggested that 2,4,5-TMPEA may actually be inactive as a psychedelic in animals and humans. [13]

2C-D (2C-M) was the first of the 2C drugs to be discovered. [15] [16] [17] [18] It was synthesized and studied in animals by Ho and colleagues and they published their findings in 1970. [15] [16] [17] [18] Alexander Shulgin synthesized 2C-B and 2C-D in 1974 and discovered their psychedelic effects in self-experiments conducted in 1974 and 1975. [1] [19] [15] [16] [20] He published his findings in the scientific literature in 1975. [1] [19] [15] [16] [20] 2C-I was first described by Shulgin and colleagues in 1977 and initial psychoactivity was reported by Shulgin in 1978. [13] [21] Shulgin also first synthesized 2C-E in 1977. [22] [23] Subsequently, numerous other 2C drugs have been synthesized and characterized. [5] [24] [15] [1] [19]

2C-B gained popularity as a recreational drug and MDMA alternative in the mid-1980s and became a controlled substance in the United States in 1994. [1] [3] It is said to be the most popular of the 2C drugs. [3]

List of 2C drugs [1]

NomenclatureR3R42D StructureCAS number
2C-B H Br 2C-B.svg 66142-81-2
2C-Bn H CH2C6H5 2C-Bn structure.png
2C-Bu H CH2CH2CH2CH3 2C-Bu structure.png
2C-C H Cl 2C-C.svg 88441-14-9
2C-C-3 [25] Cl Cl 2CC3 structure.png
2C-CN H C≡N 2C-CN structure.png 88441-07-0
2C-D H CH3 2C-D-Chemdraw.png 24333-19-5
2C-E H CH2CH3 2C-E-Chemdraw.png 71539-34-9
2C-EF HCH2CH2F 2C-EF.svg 1222814-77-8
2C-F H F 2C-F-Chemdraw.png 207740-15-6
2C-G CH3CH3 2C-G-Chemdraw.png 207740-18-9
2C-G-1 CH2 2C-G-1.png
2C-G-2 (CH2)2 2C-G-2.png
2C-G-3 (CH2)3 2C-G-3-Chemdraw.png 207740-19-0
2C-G-4 (CH2)4 2C-G-4-Chemdraw.png 952006-59-6
2C-G-5 (CH2)5 2C-G-5.svg 207740-20-3
2C-G-6 (CH2)6 2C-G-6.png
2C-G-N (CH)4 2C-G-N-Chemdraw.png 207740-21-4
2C-H HH 2C-H-Chemdraw.png 3600-86-0
2C-I H I 2C-I-Chemdraw.png 69587-11-7
2C-iP H CH(CH3)2 2C-iP structure.png 1498978-47-4
2C-TBUH C(CH3)3 2C-TBU structure.png
2C-CP H C3H5 2C-cP.svg 2888537-46-8
2C-CPEH C5H9 2C-CPE structure.png
2C-N H NO2 2C-N-Chemdraw.png 261789-00-8
2C-NH2 H NH2 2C-NH2 structure.png 168699-66-9
2C-PYRH Pyrrolidine 2C-PYR structure.png
2C-PIPH Piperidine 2C-PIP structure.png
2C-O H OCH3 2C-O-Chemdraw.png 15394-83-9
2C-O-4 H OCH(CH3)2 2C-O-4-Chemdraw.png 952006-65-4
2C-MOM [26] H CH2OCH3 2C-MOM structure.png
2C-P H CH2CH2CH3 2C-P2DACS.svg 207740-22-5
2C-Ph H C6H5 2C-Ph structure.png
2C-Se H Se CH3 2C-SE-Chemdraw.png 1189246-68-1
2C-T H SCH3 2C-T-Chemdraw.png 61638-09-3
2C-T-2 HSCH2CH3 2C-T-2-Chemdraw.png 207740-24-7
2C-T-3 [27] HSCH2C(=CH2)CH3 2C-T-3.svg 648957-40-8
2C-T-4 HSCH(CH3)2 2C-T-4-Chemdraw.png 207740-25-8
2C-T-5 [27] 2CT5 structure.png
2C-T-6 [27] 2CT6 structure.png
2C-T-7 HS(CH2)2CH3 2C-T-7-Chemdraw.png 207740-26-9
2C-T-8 HSCH2CH(CH2)2 2C-T-8-Chemdraw.png 207740-27-0
2C-T-9 [27] 2CT9 structure.png 207740-28-1
2C-T-10 [27] 2CT10 structure.png
2C-T-11 [27] 2CT11 structure.png
2C-T-12 [27] 2CT12 structure.png
2C-T-13 HS(CH2)2OCH3 2C-T-13.svg 207740-30-5
2C-T-14 [27] 2CT14 structure.png
2C-T-15 HSCH(CH2)2 2C-T-15-Chemdraw.png
2C-T-16 [28] HSCH2CH=CH2 2CT16 structure.png 648957-42-0
2C-T-17 HSCH(CH3)CH2CH3 2C-T-17-Chemdraw.png 207740-32-7
2C-T-18 [27] 2CT18 structure.png
2C-T-19 HSCH2CH2CH2CH3 2C-T-9-Chemdraw.png
2C-T-21 HS(CH2)2F 2C-T-21-Chemdraw.png 207740-33-8
2C-T-21.5 [27] 2CT21.5 structure.png 648957-46-4
2C-T-22 [27] 2CT22 structure.png 648957-48-6
2C-T-23 [27] 2CT23 structure.png
2C-T-24 [27] 2CT24 structure.png
2C-T-25 [27] 2CT25 structure.png
2C-T-27 [27] 2CT27 structure.png 648957-52-2
2C-T-28 [27] 2CT28 structure.png 648957-54-4
2C-T-30 [27] 2CT30 structure.png
2C-T-31 [27] 2CT31 structure.png
2C-T-32 [27] 2CT32 structure.png
2C-T-33 [27] 2CT33 structure.png
2C-T-DFMHSCF2H 2C-T-DFM structure.png
CYB210010 [29] HSCF3 CYB210010 structure.png
2C-T-DFPHSCH2CH2CF2H 2C-T-DFP structure.png
2C-T-PARGYHSCH2C≡CH 2C-T-PARGY structure.png
2C-DFM [30] : 770 HCHF2 2C-DFM structure.png
2C-TFM H CF3 2C-TFM-Chemdraw.png 159277-08-4
2C-TFE HCH2CF3 2C-TFE structure.png
2C-PFEHCF2CF3 2C-PFE structure.png
2C-PFSHSF5 2C-PFS structure.png
2C-YN H C≡CH 2C-YN skeletal.svg 752982-24-4
2C-V H CH=CH2 2C-V structure.png
2C-AL [31] H CH2CH=CH2 2C-AL structure.png

Legality

Canada

As of October 12, 2016, the 2C-x family of substituted phenethylamines is a controlled substance (Schedule III) in Canada. [32]

See also

Related Research Articles

<span class="mw-page-title-main">2C-B</span> Psychoactive drug

2C-B (4-bromo-2,5-dimethoxyphenethylamine), also known as Nexus, is a synthetic psychedelic drug of the 2C family, mainly used as a recreational drug. It was first synthesized by Alexander Shulgin in 1974 for use in psychotherapy. To date, there is limited scientific information regarding the drug's pharmacokinetics and pharmacological effects in humans. The existing studies primarily classify 2C-B as a stimulant and hallucinogen, and less commonly an entactogen and empathogen.

<span class="mw-page-title-main">2C-T-2</span> Chemical compound

2C-T-2 is a psychedelic and entactogenic phenethylamine of the 2C family. It was first synthesized in 1981 by Alexander Shulgin, and rated by him as one of the "magical half-dozen" most important psychedelic phenethylamine compounds. The drug has structural and pharmacodynamic properties similar to those of 2C-T-7.

<span class="mw-page-title-main">2,5-Dimethoxy-4-methylamphetamine</span> Chemical compound

2,5-Dimethoxy-4-methylamphetamine is a psychedelic and a substituted amphetamine. It was first synthesized by Alexander Shulgin, and later reported in his book PiHKAL: A Chemical Love Story. DOM is classified as a Schedule I substance in the United States, and is similarly controlled in other parts of the world. Internationally, it is a Schedule I drug under the Convention on Psychotropic Substances. It is generally taken orally.

<span class="mw-page-title-main">2,5-Dimethoxy-4-bromoamphetamine</span> Chemical compound

Dimethoxybromoamphetamine (DOB), also known as brolamfetamine 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.

<span class="mw-page-title-main">2C-T-8</span> Chemical compound

2C-T-8 is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an entheogen.

<span class="mw-page-title-main">2,5-Dimethoxy-4-iodoamphetamine</span> Chemical compound

2,5-Dimethoxy-4-iodoamphetamine (DOI) is a psychedelic drug of the amphetamine and 4-substituted-2,5-dimethoxyamphetamine (DOx) families.

<span class="mw-page-title-main">2C-T</span> Chemical compound

2C-T is a psychedelic and hallucinogenic drug of the 2C family. It is used by some as an entheogen. It has structural and pharmacodynamic properties similar to the drugs mescaline and 2C-T-2.

<span class="mw-page-title-main">2C-TFM</span> Psychedelic phenethylamine drug

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.

<span class="mw-page-title-main">2,5-Dimethoxy-4-ethylamphetamine</span> Psychedelic drug

2,5-Dimethoxy-4-ethylamphetamine (DOET) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families. It is closely related to DOM and is a synthetic analogue of the naturally occurring phenethylamine psychedelic mescaline. The drug acts as a selective agonist of the serotonin 5-HT2 receptors, including of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.

<span class="mw-page-title-main">Aleph (psychedelic)</span> Chemical compound

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.

<span class="mw-page-title-main">2C-H</span> Chemical compound

2C-H (2,5-dimethoxyphenethylamine) is a lesser-known substituted phenethylamine of the 2C family.

<span class="mw-page-title-main">Ariadne (drug)</span> Psychoactive phenethylamine drug

Ariadne, also known chemically as 4C-D or 4C-DOM, by its developmental code name BL-3912, and by its former tentative brand name Dimoxamine, is a little-known psychoactive drug of the phenethylamine, amphetamine, and phenylisobutylamine families. It is a homologue of the psychedelics 2C-D and DOM.

<span class="mw-page-title-main">2,5-Dimethoxy-4-butylamphetamine</span> Substituted amphetamine psychedelic drug

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 , only low dosages of 2 to 3 mg were tested, with the duration simply listed as "very long". DOBU produces paresthesia and difficulty sleeping, but with few other effects.

<span class="mw-page-title-main">2,5-Dimethoxy-4-amylamphetamine</span> Chemical compound

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 , the minimum dosage is listed as 10 mg, and the duration is unknown. DOAM produces a bare threshold and tenseness.

<span class="mw-page-title-main">2,5-Dimethoxy-4-trifluoromethylamphetamine</span> Psychedelic drug

2,5-Dimethoxy-4-trifluoromethylamphetamine (DOTFM) is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized in 1994 by a team at Purdue University led by David E. Nichols. DOTFM is the alpha-methylated analogue of 2C-TFM, and is around twice as potent in animal studies. It acts as an agonist at the 5-HT2A and 5-HT2C receptors. In drug-substitution experiments in rats, DOTFM fully substituted for LSD and was slightly more potent than DOI.

<span class="mw-page-title-main">2,5-Dimethoxy-4-fluoroamphetamine</span> Chemical compound

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.

DO<i>x</i> Class of chemical compounds

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. They are 4-substituted derivatives of 2,5-dimethoxyamphetamine.

<span class="mw-page-title-main">2C-T-16</span> Psychedelic drug

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.

<span class="mw-page-title-main">25-NB</span> Family of serotonergic psychedelics

The 25-NB (25x-NBx) series, or NBOMe series, also known as the N-benzylphenethylamines, is a family of serotonergic psychedelics. They are substituted phenethylamines and were derived from the 2C family. The most commonly encountered NBOMe drugs are 25I-NBOMe, 25B-NBOMe, and 25C-NBOMe.

<span class="mw-page-title-main">CYB210010</span> Chemical compound

CYB210010, also known as 2C-T-TFM, is a lesser-known psychedelic drug of the phenethylamine family related to compounds such as 2C-T and 2C-T-21.

References

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  28. ↑ Daniel Trachsel (2003). "Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 2. 4-Thio-substituted [2-(2,5-dimethoxyphenyl)ethyl]amines (=2,5-dimethoxybenzeneethanamines)". Helvetica Chimica Acta . 86 (7): 2610–2619. doi:10.1002/hlca.200390210.
  29. ↑ Varty GB, Canal CE, Mueller TA, Hartsel JA, Tyagi R, Avery K, Morgan ME, Reichelt AC, Pathare P, Stang E, Palfreyman MG, Nivorozhkin A. Synthesis and Structure-Activity Relationships of 2,5-Dimethoxy-4-Substituted Phenethylamines and the Discovery of CYB210010: A Potent, Orally Bioavailable and Long-Acting Serotonin 5-HT2 Receptor Agonist. J Med Chem. 2024 Apr 25;67(8):6144-6188. doi : 10.1021/acs.jmedchem.3c01961 PMID   38593423
  30. ↑ Daniel Trachsel; David Lehmann & Christoph Enzensperger (2013). Phenethylamine: Von der Struktur zur Funktion. Nachtschatten Verlag AG. ISBN   978-3-03788-700-4.
  31. ↑ Kruegel AC. Phenalkylamines and Methods of Treating Mood Disorders. Patent WO 2022/006186
  32. ↑ "Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". Canada Gazette . April 15, 2016. Retrieved August 28, 2016.
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