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2C (psychedelics)

Family of phenethylamine psychedelics From Wikipedia, the free encyclopedia

2C (psychedelics)

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]

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General structure of a 2C compound

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]

Use

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Perspective

The 2C drugs are orally active, are used at oral doses of 6 to 150 mg depending on the drug, and have durations of 3 to 48 hours depending on the drug.[1][6][5][7] However, many have doses in the range of 10 to 60 mg and durations in the range of 4 to 12 hours.[1] The 2C drugs produce psychedelic effects.[1][5][8][3] Some, such as 2C-B, have also been reported to have some entactogenic qualities, though findings appear to be mixed.[8][3][9][10]

More information Compound, Chemical name ...
Doses and durations of 2C drugs
CompoundChemical nameDosageDuration
2C-AL4-Allyl-2,5-dimethoxyphenethylamineUnknownUnknown
2C-B4-Bromo-2,5-dimethoxyphenethylamine10–35 mg4–8 hours
2C-Bu4-Butyl-2,5-dimethoxyphenethylamineUnknownUnknown
2C-C4-Chloro-2,5-dimethoxyphenethylamine20–40 mg4–8 hours
2C-CN4-Cyano-2,5-dimethoxyphenethylamine>22 mgUnknown
2C-CP4-Cyclopropyl-2,5-dimethoxyphenethylamine15–35 mg3–6 hours
2C-D4-Methyl-2,5-dimethoxyphenethylamine20–60 mg4–6 hours
2C-E4-Ethyl-2,5-dimethoxyphenethylamine10–25 mg6–12 hours
2C-EF4-Fluoroethyl-2,5-dimethoxyphenethylamine10–25 mgUnknown
2C-F4-Fluoro-2,5-dimethoxyphenethylamine≥250 mgUnknown
2C-G3,4-Dimethyl-2,5-dimethoxyphenethylamine20–35 mg18–30 hours
2C-G-33,4-Trimethylene-2,5-dimethoxyphenethylamine16–25 mg12–24 hours
2C-G-53,4-Norbornyl-2,5-dimethoxyphenethylamine10–16 mg32–48 hours
2C-H2,5-DimethoxyphenethylamineUnknownUnknown
2C-I4-Iodo-2,5-dimethoxyphenethylamine14–22 mg6–10 hours
2C-iBu4-Isobutyl-2,5-dimethoxyphenethylamine≥5 mg~20 hours
2C-iP4-Isopropyl-2,5-dimethoxyphenethylamine8–25 mg8–12 hours
2C-N4-Nitro-2,5-dimethoxyphenethylamine100–150 mg4–6 hours
2C-O4-Methoxy-2,5-dimethoxyphenethylamineUnknownUnknown
2C-O-44-Isopropoxy-2,5-dimethoxyphenethylamine>60 mgUnknown
2C-O-224-(2,2,2-Trifluoroethoxy)-2,5-dimethoxyphenethylamine≥57 mgUnknown
2C-P4-Propyl-2,5-dimethoxyphenethylamine6–10 mg5–16 hours
2C-Ph (2C-BI-1)4-Phenyl-2,5-dimethoxyphenethylamineUnknownUnknown
2C-SE4-Methylseleno-2,5-dimethoxyphenethylamine~100 mg6–8 hours
2C-T (2C-T-1)4-Methylthio-2,5-dimethoxyphenethylamine60–100 mg3–5 hours
2C-T-24-Ethylthio-2,5-dimethoxyphenethylamine12–25 mg6–8 hours
2C-T-3 (2C-T-20)4-Methallylthio-2,5-dimethoxyphenethylamine15–40 mg8–14 hours
2C-T-44-Isopropylthio-2,5-dimethoxyphenethylamine8–20 mg12–18 hours
2C-T-74-Propylthio-2,5-dimethoxyphenethylamine10–30 mg8–15 hours
2C-T-84-Cyclopropylmethylthio-2,5-dimethoxyphenethylamine30–50 mg10–15 hours
2C-T-94-tert-Butylthio-2,5-dimethoxyphenethylamine60–100 mg12–18 hours
2C-T-134-(2-Methoxyethylthio)-2,5-dimethoxyphenethylamine25–40 mg6–8 hours
2C-T-154-Cyclopropylthio-2,5-dimethoxyphenethylamine>30 mgSeveral hours
2C-T-164-Allylthio-2,5-dimethoxyphenethylamine10–25 mg4–6 hours
2C-T-174-sec-Butylthio-2,5-dimethoxyphenethylamine60–100 mg10–15 hours
2C-T-194-Butylthio-2,5-dimethoxyphenethylamineUnknownUnknown
2C-T-214-(2-Fluoroethylthio)-2,5-dimethoxyphenethylamine8–20 mg7–10 hours
2C-T-21.54-(2,2-Difluoroethylthio)-2,5-dimethoxyphenethylamine12–30 mg8–14 hours
2C-T-224-(2,2,2-Trifluoroethylthio)-2,5-dimethoxyphenethylamineUnknownUnknown
2C-T-254-Isobutylthio-2,5-dimethoxyphenethylamine>30 mgUnknown
2C-T-274-Benzylthio-2,5-dimethoxyphenethylamine≥80 mgUnknown
2C-T-284-(3-Fluoropropylthio)-2,5-dimethoxyphenethylamine8–20 mg8–10 hours
2C-T-304-(4-Fluorobutylthio)-2,5-dimethoxyphenethylamineUnknownUnknown
2C-T-334-(3-Methoxybenzylthio)-2,5-dimethoxyphenethylamineUnknownUnknown
2C-T-36 (2C-T-TFM)4-Trifluoromethylthio-2,5-dimethoxyphenethylamineUnknownUnknown
2C-tBu4-tert-Butyl-2,5-dimethoxyphenethylamine>5–10 mgUnknown
2C-TFE4-(2,2,2-Trifluoroethyl)-2,5-dimethoxyphenethylamine5–15 mg12–24 hours
2C-TFM4-Trifluoromethyl-2,5-dimethoxyphenethylamine3–6 mg≥5–10 hours
2C-V4-Ethenyl-2,5-dimethoxyphenethylamine~25 mg~5 hours
2C-YN4-Ethynyl-2,5-dimethoxyphenethylamine~50 mg~2 hours
Refs: [1][6][3][7][5][2][11][12][13][4]
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Pharmacology

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Perspective

Pharmacodynamics

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The 2C drugs act as agonists of the serotonin 5-HT2 receptors, including of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.[14][15][16][17][18] They are partial agonists of the serotonin 5-HT2A receptor.[14][15] Most of the 2C drugs have much lower affinity for the serotonin 5-HT1A receptor than for the serotonin 5-HT2A receptor.[14][15][16][17] Most of the 2C drugs have also shown about 5- to 15-fold higher affinity for the serotonin 5-HT2A receptor over the serotonin 5-HT2C receptor and about 15- to 100-fold higher affinity for the serotonin 5-HT2A receptor over the serotonin 5-HT1A receptor.[15] The psychedelic effects of the 2C drugs are thought to be mediated specifically by activation of the serotonin 5-HT2A receptor.[14][16][18]

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.[14][19][16][15][18] Most of the 2C drugs are agonists of the rat and mouse trace amine-associated receptor 1 (TAAR1).[14][20][21][15] However, most are inactive as agonists of the human TAAR1.[14][20][21][15] The 2C drugs show very weak monoamine oxidase inhibition, including of monoamine oxidase A (MAO-A) and/or monoamine oxidase B (MAO-B).[14]

More information Drug, 5-HT1A ...
2C drugs at serotonin 5-HT1 and 5-HT2 receptors
Drug5-HT1A5-HT1B5-HT2A5-HT2B5-HT2C
Ki (nM)EC50 (nM)Emax (%)Ki (nM)Ki (nM)EC50 (nM)Emax (%)Ki (nM)EC50 (nM)Emax (%)Ki (nM)EC50 (nM)Emax (%)
2C-B240–311NDND104.46.9–27.61.89–805–99%13.575–13052–89%43–89.50.031–0.264104–116%
2C-C190–740>10,000<25%252.95.47–139.27–20049–102%ND28081%5.4–9024.294%
2C-D440–1,630>10,000<25%ND23.9–32.443.5–35041–125%ND23077%12.7–15071.1100%
2C-E307.3–1,190>10,000<25%ND4.50–43.92.5–11040–125%25.119066%5.4–104.10.233–18.098–106%
2C-H70NDNDND1,6002,408–9,40028–67%ND6,20046%4,100NDND
2C-I180–9704,900102%ND3.5–9.33.83–6015–82%ND15070%10.2–402.879–100%
2C-N2,200NDNDND23.517020–48%ND73074%370ND40–50%
2C-P110NDNDND8.19063%ND13072%40NDND
2C-T-11,035NDNDND492.075%ND5758%347NDND
2C-T-2370–1,7403,00076%857.59–39.90.354–8067–128%613075%14.2–690.0233–3.887–107%
2C-T-4470–916NDNDND27.9–545.5–22056–87%ND63–16068–75%180–295NDND
2C-T-7520–878NDNDND5.3–6.51.2–13049–101%ND52–35045–75%39–54NDND
Notes: The smaller the value, the more avidly the drug binds to or activates the site. Refs: [15][16][17][14][22][23][24]
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Effects

In accordance with their psychedelic effects in humans, the 2C drugs produce the head-twitch response and wet dog shakes, behavioral proxies of psychedelic effects, in rodents.[14] At least some 2C drugs, such as 2C-D and 2C-E, produce hyperlocomotion at lower doses in rodents.[14] All 2C drugs produce hypolocomotion at higher doses in rodents.[14] 2C drugs, including 2C-C, 2C-D, 2C-E, and 2C-I, substitute partially to fully for psychedelics like DOM, DMT, and LSD and/or for the entactogen MDMA in rodent drug discrimination tests.[14][16] However, none of the assessed 2C drugs substituted for dextromethamphetamine, suggesting that they lack amphetamine-type or stimulant-like effects.[14][16]

In contrast to most psychedelics, at least two assessed 2C drugs, 2C-C and 2C-P, have shown reinforcing effects in rodents, including conditioned place preference (CPP) and self-administration.[14][25] The mechanism by which these effects are mediated is unknown.[14] However, it may be related to reduced expression of the dopamine transporter (DAT) and increased DAT phosphorylation, in turn resulting in increased extracellular dopamine levels in certain brain areas.[14][25] These 2C drugs might have misuse potential in humans.[14][25] Similar reinforcing effects in animals have been observed for NBOMe analogues of 2C drugs, including 25B-NBOMe, 25D-NBOMe, 25E-NBOMe, 25H-NBOMe, and 25N-NBOMe.[14][26][27][28][29][30][31]

Similarly to DOI, tolerance has been found to gradually develop to the head-twitch response induced by 2C-T-7 with chronic administration in rodents.[14]

Various 2C drugs show potent anti-inflammatory effects mediated by serotonin 5-HT2A receptor activation.[32] Among these include 2C-I, 2C-B, 2C-H, and 2C-iBu.[32][33] Others, such as 2C-B-Fly and 2C-T-33, were less effective.[32] 2C-iBu has shown a greater separation between anti-inflammatory effects and psychedelic-like effects in animals than other 2C drugs and is being investigated for possible use as a pharmaceutical drug.[33][34]

Pharmacokinetics

The 2C drugs are orally active.[1] They are metabolized by O-demethylation and deamination.[1][35] This is mediated specifically by monoamine oxidase (MAO) enzymes MAO-A and MAO-B, whereas cytochrome P450 enzymes appear to metabolize only some 2C drugs and to have only a very small role.[35]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

The 2C drugs are metabolized by the monoamine oxidase (MAO) enzymes, including both MAO-A and MAO-B.[1][35] As a result, they may be potentiated by monoamine oxidase inhibitors (MAOIs), such as phenelzine, tranylcypromine, moclobemide, and selegiline.[1][35][36] This may lead to overdose and serious toxicity.[1][35][36]

History

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Perspective
See also: DOx § 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).[37][38] He published his findings in 1931.[37][38] 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.[37]

2C-D (2C-M) was the first of the 2C drugs besides 2C-O to be discovered.[2][39][40][41] It was synthesized and studied in animals by Ho and colleagues and they published their findings in 1970.[2][39][40][41] Alexander Shulgin synthesized 2C-B and 2C-D in 1974 and discovered their psychedelic effects in self-experiments conducted in 1974 and 1975.[1][42][2][39][43] He published his findings in the scientific literature in 1975.[1][42][2][39][43] 2C-T was first described by Shulgin and David E. Nichols in 1976.[44] 2C-I was first described by Shulgin and colleagues in 1977 and initial psychoactivity was reported by Shulgin in 1978.[37][45] Shulgin also first synthesized 2C-E in 1977.[46][47] Subsequently, numerous other 2C drugs have been synthesized and characterized.[5][6][2][1][42]

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]

Legal status

Canada

As of October 12, 2016, the 2C-x family of substituted phenethylamines is a controlled substance (Schedule III) in Canada.[48]

List of 2C drugs

More information Name, R3 ...
Name R3 R4 Structure CAS #
2C-B H Br Thumb 66142-81-2
2C-Bn H CH2C6H5 Thumb
2C-Bu H CH2CH2CH2CH3 Thumb
2C-C H Cl Thumb 88441-14-9
2C-C-3 [49] Cl Cl Thumb
2C-CN H C≡N Thumb 88441-07-0
2C-D H CH3 Thumb 24333-19-5
2C-E H CH2CH3 Thumb 71539-34-9
2C-EF H CH2CH2F Thumb 1222814-77-8
2C-F H F Thumb 207740-15-6
2C-G CH3 CH3 Thumb 207740-18-9
2C-G-1 CH2 Thumb
2C-G-2 (CH2)2 Thumb
2C-G-3 (CH2)3 Thumb 207740-19-0
2C-G-4 (CH2)4 Thumb 952006-59-6
2C-G-5 (CH2)5 Thumb 207740-20-3
2C-G-6 (CH2)6 Thumb
2C-G-N (CH)4 Thumb 207740-21-4
2C-H H H Thumb 3600-86-0
2C-I H I Thumb 69587-11-7
2C-iBu H iBu Thumb
2C-iP H CH(CH3)2 Thumb 1498978-47-4
2C-tBu H C(CH3)3 Thumb
2C-CP H C3H5 Thumb 2888537-46-8
2C-CPE H C5H9 Thumb
2C-N H NO2 Thumb 261789-00-8
2C-NH2 H NH2 Thumb 168699-66-9
2C-PYR H Pyrrolidine Thumb
2C-PIP H Piperidine Thumb
2C-O H OCH3 Thumb 15394-83-9
2C-O-4 H OCH(CH3)2 Thumb 952006-65-4
2C-MOM [50] H CH2OCH3 Thumb
2C-P H CH2CH2CH3 Thumb 207740-22-5
2C-Ph (2C-BI-1) H C6H5 Thumb
2C-Se H Se CH3 Thumb 1189246-68-1
2C-T H SCH3 Thumb 61638-09-3
2C-T-2 H SCH2CH3 Thumb 207740-24-7
2C-T-3[51] H SCH2C(=CH2)CH3 Thumb 648957-40-8
2C-T-4 H SCH(CH3)2 Thumb 207740-25-8
2C-T-5[51] Thumb
2C-T-6[51] Thumb
2C-T-7 H S(CH2)2CH3 Thumb 207740-26-9
2C-T-8 H SCH2CH(CH2)2 Thumb 207740-27-0
2C-T-9[51] Thumb 207740-28-1
2C-T-10[51] Thumb
2C-T-11[51] Thumb
2C-T-12[51] Thumb
2C-T-13 H S(CH2)2OCH3 Thumb 207740-30-5
2C-T-14[51] Thumb
2C-T-15 H SCH(CH2)2 Thumb
2C-T-16[52] H SCH2CH=CH2 Thumb 648957-42-0
2C-T-17 H SCH(CH3)CH2CH3 Thumb 207740-32-7
2C-T-18[51] Thumb
2C-T-19 H SCH2CH2CH2CH3 Thumb
2C-T-21 H S(CH2)2F Thumb 207740-33-8
2C-T-21.5[51] Thumb 648957-46-4
2C-T-22[51] Thumb 648957-48-6
2C-T-23[51] Thumb
2C-T-24[51] Thumb
2C-T-25[51] Thumb
2C-T-27[51] Thumb 648957-52-2
2C-T-28[51] Thumb 648957-54-4
2C-T-30[51] Thumb
2C-T-31[51] Thumb
2C-T-32[51] Thumb
2C-T-33[51] Thumb
2C-T-DFM H SCF2H Thumb
CYB210010 (2C-T-TFM)[53] H SCF3 Thumb
2C-T-DFP H SCH2CH2CF2H Thumb
2C-T-PARGY H SCH2C≡CH Thumb
2C-DFM [4]: 770  H CHF2 Thumb
2C-TFM H CF3 Thumb 159277-08-4
2C-TFE H CH2CF3 Thumb
2C-PFE H CF2CF3 Thumb
2C-PFS H SF5 Thumb
2C-YN H C≡CH Thumb 752982-24-4
2C-V H CH=CH2 Thumb
2C-AL[54] H CH2CH=CH2 Thumb
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Related compounds

More information Name, Chemical name ...
Name Chemical name Structure Ref
XOB N-[(4-Phenylbutoxy)hexyl]-4-bromo-2,5-dimethoxyphenethylamine Thumb [55]
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See also

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