2C (psychedelics)

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Template:Short description

File: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]

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

The 2C drugs are orally active, are used at oral doses of 6 to 150Script error: No such module "String".mg depending on the drug, and have durations of 3 to 48Script error: No such module "String".hours depending on the drug.[1][6][5][7] However, many have doses in the range of 10 to 60Script error: No such module "String".mg and durations in the range of 4 to 12Script error: No such module "String".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]

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Doses and durations of 2C drugs
Compound Chemical name Dosage Duration
2C-AL 4-Allyl-2,5-dimethoxyphenethylamine Unknown Unknown
2C-B 4-Bromo-2,5-dimethoxyphenethylamine 10–35 mg 4–8 hours
2C-Bu 4-Butyl-2,5-dimethoxyphenethylamine Unknown Unknown
2C-C 4-Chloro-2,5-dimethoxyphenethylamine 20–40 mg 4–8 hours
2C-CN 4-Cyano-2,5-dimethoxyphenethylamine >22 mg Unknown
2C-CP 4-Cyclopropyl-2,5-dimethoxyphenethylamine 15–35 mg 3–6 hours
2C-D 4-Methyl-2,5-dimethoxyphenethylamine 20–60 mg 4–6 hours
2C-E 4-Ethyl-2,5-dimethoxyphenethylamine 10–25 mg 6–12 hours
2C-EF 4-Fluoroethyl-2,5-dimethoxyphenethylamine 10–25 mg Unknown
2C-F 4-Fluoro-2,5-dimethoxyphenethylamine ≥250 mg Unknown
2C-G 3,4-Dimethyl-2,5-dimethoxyphenethylamine 20–35 mg 18–30 hours
2C-G-3 3,4-Trimethylene-2,5-dimethoxyphenethylamine 16–25 mg 12–24 hours
2C-G-5 3,4-Norbornyl-2,5-dimethoxyphenethylamine 10–16 mg 32–48 hours
2C-H 2,5-Dimethoxyphenethylamine Unknown Unknown
2C-I 4-Iodo-2,5-dimethoxyphenethylamine 14–22 mg 6–10 hours
2C-iBu 4-Isobutyl-2,5-dimethoxyphenethylamine ≥5 mg ~20 hours
2C-iP 4-Isopropyl-2,5-dimethoxyphenethylamine 8–25 mg 8–12 hours
2C-N 4-Nitro-2,5-dimethoxyphenethylamine 100–150 mg 4–6 hours
2C-O 4-Methoxy-2,5-dimethoxyphenethylamine Unknown Unknown
2C-O-4 4-Isopropoxy-2,5-dimethoxyphenethylamine >60 mg Unknown
2C-O-22 4-(2,2,2-Trifluoroethoxy)-2,5-dimethoxyphenethylamine ≥57 mg Unknown
2C-P 4-Propyl-2,5-dimethoxyphenethylamine 6–10 mg 5–16 hours
2C-Ph (2C-BI-1) 4-Phenyl-2,5-dimethoxyphenethylamine Unknown Unknown
2C-SE 4-Methylseleno-2,5-dimethoxyphenethylamine ~100 mg 6–8 hours
2C-T (2C-T-1) 4-Methylthio-2,5-dimethoxyphenethylamine 60–100 mg 3–5 hours
2C-T-2 4-Ethylthio-2,5-dimethoxyphenethylamine 12–25 mg 6–8 hours
2C-T-3 (2C-T-20) 4-Methallylthio-2,5-dimethoxyphenethylamine 15–40 mg 8–14 hours
2C-T-4 4-Isopropylthio-2,5-dimethoxyphenethylamine 8–20 mg 12–18 hours
2C-T-7 4-Propylthio-2,5-dimethoxyphenethylamine 10–30 mg 8–15 hours
2C-T-8 4-Cyclopropylmethylthio-2,5-dimethoxyphenethylamine 30–50 mg 10–15 hours
2C-T-9 4-tert-Butylthio-2,5-dimethoxyphenethylamine 60–100 mg 12–18 hours
2C-T-13 4-(2-Methoxyethylthio)-2,5-dimethoxyphenethylamine 25–40 mg 6–8 hours
2C-T-15 4-Cyclopropylthio-2,5-dimethoxyphenethylamine >30 mg Several hours
2C-T-16 4-Allylthio-2,5-dimethoxyphenethylamine 10–25 mg 4–6 hours
2C-T-17 4-sec-Butylthio-2,5-dimethoxyphenethylamine 60–100 mg 10–15 hours
2C-T-19 4-Butylthio-2,5-dimethoxyphenethylamine Unknown Unknown
2C-T-21 4-(2-Fluoroethylthio)-2,5-dimethoxyphenethylamine 8–20 mg 7–10 hours
2C-T-21.5 4-(2,2-Difluoroethylthio)-2,5-dimethoxyphenethylamine 12–30 mg 8–14 hours
2C-T-22 4-(2,2,2-Trifluoroethylthio)-2,5-dimethoxyphenethylamine Unknown Unknown
2C-T-25 4-Isobutylthio-2,5-dimethoxyphenethylamine >30 mg Unknown
2C-T-27 4-Benzylthio-2,5-dimethoxyphenethylamine ≥80 mg Unknown
2C-T-28 4-(3-Fluoropropylthio)-2,5-dimethoxyphenethylamine 8–20 mg 8–10 hours
2C-T-30 4-(4-Fluorobutylthio)-2,5-dimethoxyphenethylamine Unknown Unknown
2C-T-33 4-(3-Methoxybenzylthio)-2,5-dimethoxyphenethylamine Unknown Unknown
2C-T-36 (2C-T-TFM) 4-Trifluoromethylthio-2,5-dimethoxyphenethylamine Unknown Unknown
2C-tBu 4-tert-Butyl-2,5-dimethoxyphenethylamine >5–10 mg Unknown
2C-TFE 4-(2,2,2-Trifluoroethyl)-2,5-dimethoxyphenethylamine 5–15 mg 12–24 hours
2C-TFM 4-Trifluoromethyl-2,5-dimethoxyphenethylamine 3–6 mg ≥5–10 hours
2C-V 4-Ethenyl-2,5-dimethoxyphenethylamine ~25 mg ~5 hours
2C-YN 4-Ethynyl-2,5-dimethoxyphenethylamine ~50 mg ~2 hours
Refs: [1][6][3][7][5][2][11][12][13][4]

Interactions

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The 2C drugs are metabolized by the monoamine oxidase (MAO) enzymes, including both MAO-A and MAO-B.[1][14] As a result, they may be potentiated by monoamine oxidase inhibitors (MAOIs), such as phenelzine, tranylcypromine, moclobemide, and selegiline.[1][14][15] This may lead to overdose and serious toxicity.[1][14][15]

Pharmacology

Pharmacodynamics

Actions

The 2C drugs act as agonists of the serotonin 5-HT2 receptors, including of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.[16][17][18][19][20] They are partial agonists of the serotonin 5-HT2A receptor.[16][17] Most of the 2C drugs have much lower affinity for the serotonin 5-HT1A receptor than for the serotonin 5-HT2A receptor.[16][17][18][19] 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.[17] The psychedelic effects of the 2C drugs are thought to be mediated specifically by activation of the serotonin 5-HT2A receptor.[16][18][20]

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.[16][21][18][17][20] Most of the 2C drugs are agonists of the rat and mouse trace amine-associated receptor 1 (TAAR1).[16][22][23][17] However, most are inactive as agonists of the human TAAR1.[16][22][23][17] The 2C drugs show very weak monoamine oxidase inhibition, including of monoamine oxidase A (MAO-A) and/or monoamine oxidase B (MAO-B).[16]

2C drugs at serotonin 5-HT1 and 5-HT2 receptors
Drug 5-HT1A 5-HT1B 5-HT2A 5-HT2B 5-HT2C
Ki (nM) EC50 (nM) Emax (%) Ki (nM) Ki (nM) EC50 (nM) Emax (%) Ki (nM) EC50 (nM) Emax (%) Ki (nM) EC50 (nM) Emax (%)
2C-B 130–311 ND ND 104.4 6.9–27.6 1.89–80 5–99% 13.5 75–130 52–89% 43–89.5 0.031–0.264 104–116%
2C-C 190–740 >10,000 <25% 252.9 5.47–13 9.27–200 49–102% ND 280 81% 5.4–90 24.2 94%
2C-D 440–1,630 >10,000 <25% ND 23.9–32.4 43.5–350 41–125% ND 230 77% 12.7–150 71.1 100%
2C-E 307.3–1,190 >10,000 <25% ND 4.50–43.9 2.5–110 40–125% 25.1 190 66% 5.4–104.1 0.233–18.0 98–106%
2C-H 70 ND ND ND 1,600 2,408–9,400 28–67% ND 6,200 46% 4,100 ND ND
2C-I 180–970 4,900 102% ND 3.5–9.3 3.83–60 15–82% ND 150 70% 10.2–40 2.8 79–100%
2C-N 2,200 ND ND ND 23.5 170 20–48% ND 730 74% 370 ND 40–50%
2C-P 110 ND ND ND 8.1 90 63% ND 130 72% 40 ND ND
2C-T-1 1,035 ND ND ND 49 2.0 75% ND 57 58% 347 ND ND
2C-T-2 370–1,740 3,000 76% 857.5 9–39.9 0.354–80 67–128% 6 130 75% 14.2–69 0.0233–3.8 87–107%
2C-T-4 470–916 ND ND ND 27.9–54 5.5–220 56–87% ND 63–160 68–75% 180–295 ND ND
2C-T-7 520–878 ND ND ND 5.3–6.5 1.2–130 49–101% ND 52–350 45–75% 39–54 ND ND
Notes: The smaller the value, the more avidly the drug binds to or activates the site. Refs: [17][18][19][16][24][25][26][27]

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.[16] At least some 2C drugs, such as 2C-D and 2C-E, produce hyperlocomotion at lower doses in rodents.[16] All 2C drugs produce hypolocomotion at higher doses in rodents.[16] 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.[16][18] However, none of the assessed 2C drugs substituted for dextromethamphetamine, suggesting that they lack amphetamine-type or stimulant-like effects.[16][18]

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.[16][28] The mechanism by which these effects are mediated is unknown.[16] 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.[16][28] These 2C drugs might have misuse potential in humans.[16][28] 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.[16][29][30][31][32][33][34]

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.[16]

Various 2C drugs show potent anti-inflammatory effects mediated by serotonin 5-HT2A receptor activation.[35] Among these include 2C-I, 2C-B, 2C-H, and 2C-iBu.[35][36] Others, such as 2C-B-Fly and 2C-T-33, were less effective.[35] 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.[36][37]

Pharmacokinetics

The 2C drugs are orally active.[1] They are metabolized by O-demethylation and deamination.[1][14] 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.[14]

History

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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).[38][39] He published his findings in 1931.[38][39] 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.[38]

2C-D (2C-M) was the first of the 2C drugs besides 2C-O to be discovered.[2][40][41][42] It was synthesized and studied in animals by Ho and colleagues and they published their findings in 1970.[2][40][41][42] Alexander Shulgin synthesized 2C-B and 2C-D in 1974 and discovered their psychedelic effects in self-experiments conducted in 1974 and 1975.[1][43][2][40][44] He published his findings in the scientific literature in 1975.[1][43][2][40][44] 2C-T was first described by Shulgin and David E. Nichols in 1976.[45] 2C-I was first described by Shulgin and colleagues in 1977 and initial psychoactivity was reported by Shulgin in 1978.[38][46] Shulgin also first synthesized 2C-E in 1977.[47][48] He reviewed several of these 2C drugs in 1979.[49] Subsequently, numerous other 2C drugs have been synthesized and characterized.[5][6][2][1][43]

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]

Society and culture

Legal status

Canada

As of October 12, 2016, the 2C-x family of substituted phenethylamines is a controlled substance (Schedule III) in Canada.[50]

List of 2C drugs

Template:Sticky

Name R3 R4 Structure CAS #
2C-B H Br File:2C-B.svg 66142-81-2
2C-Bn H CH2C6H5 File:2C-Bn.svg
2C-Bu H CH2CH2CH2CH3 File:2C-Bu.svg
2C-C H Cl File:2C-C.svg 88441-14-9
2C-C-3 [51] Cl Cl File:2CC3 structure.png
2C-CN H C≡N File:2C-CN.svg 88441-07-0
2C-D H CH3 File:2C-D 2DACS.svg 24333-19-5
2C-E H CH2CH3 File:2C-E-Chemdraw.png 71539-34-9
2C-EF H CH2CH2F File:2C-EF.svg 1222814-77-8
2C-F H F File:2C-F-Chemdraw.png 207740-15-6
2C-G CH3 CH3 File:2C-G-Chemdraw.png 207740-18-9
2C-G-1 CH2 File:2C-G-1.png
2C-G-2 (CH2)2 File:2C-G-2.png
2C-G-3 (CH2)3 File:2C-G-3-Chemdraw.png 207740-19-0
2C-G-4 (CH2)4 File:2C-G-4-Chemdraw.png 952006-59-6
2C-G-5 (CH2)5 File:2C-G-5.svg 207740-20-3
2C-G-6 (CH2)6 File:2C-G-6.png
2C-G-N (CH)4 File:2C-G-N-Chemdraw.png 207740-21-4
2C-H H H File:2C-H-Chemdraw.png 3600-86-0
2C-I H I File:2C-I-Chemdraw.png 69587-11-7
2C-iBu H iBu File:2C-iBu.svg
2C-iP H CH(CH3)2 File:2C-iP structure.png 1498978-47-4
2C-tBu H C(CH3)3 File:2C-TBU structure.png
2C-CP H C3H5 File:2C-cP.svg 2888537-46-8
2C-CPE H C5H9 File:2C-CPE structure.png
2C-N H NO2 File:2C-N-Chemdraw.png 261789-00-8
2C-NH2 H NH2 File:2C-NH2 structure.png 168699-66-9
2C-PYR H Pyrrolidine File:2C-PYR structure.png
2C-PIP H Piperidine File:2C-PIP structure.png
2C-O H OCH3 File:2C-O-Chemdraw.png 15394-83-9
2C-O-4 H OCH(CH3)2 File:2C-O-4-Chemdraw.png 952006-65-4
2C-MOM [52] H CH2OCH3 File:2C-MOM structure.png
2C-P H CH2CH2CH3 File:2C-P2DACS.svg 207740-22-5
2C-Ph (2C-BI-1) H C6H5 File:2C-Ph structure.png
2C-Se H Se CH3 File:2C-SE-Chemdraw.png 1189246-68-1
2C-T H SCH3 File:2C-T-Chemdraw.png 61638-09-3
2C-T-2 H SCH2CH3 File:2C-T-2-Chemdraw.png 207740-24-7
2C-T-3[53] H SCH2C(=CH2)CH3 File:2C-T-3.svg 648957-40-8
2C-T-4 H SCH(CH3)2 File:2C-T-4-Chemdraw.png 207740-25-8
2C-T-5[53] File:2CT5 structure.png
2C-T-6[53] File:2CT6 structure.png
2C-T-7 H S(CH2)2CH3 File:2C-T-7-Chemdraw.png 207740-26-9
2C-T-8 H SCH2CH(CH2)2 File:2C-T-8-Chemdraw.png 207740-27-0
2C-T-9[53] File:2CT9 structure.png 207740-28-1
2C-T-10[53] File:2CT10 structure.png
2C-T-11[53] File:2CT11 structure.png
2C-T-12[53] File:2CT12 structure.png
2C-T-13 H S(CH2)2OCH3 File:2C-T-13.svg 207740-30-5
2C-T-14[53] File:2CT14 structure.png
2C-T-15 H SCH(CH2)2 File:2C-T-15-Chemdraw.png
2C-T-16[54] H SCH2CH=CH2 File:2CT16.svg 648957-42-0
2C-T-17 H SCH(CH3)CH2CH3 File:2C-T-17-Chemdraw.png 207740-32-7
2C-T-18[53] File:2CT18 structure.png
2C-T-19 H SCH2CH2CH2CH3 File:2C-T-9-Chemdraw.png
2C-T-21 H S(CH2)2F File:2C-T-21-Chemdraw.png 207740-33-8
2C-T-21.5[53] File:2CT21.5 structure.png 648957-46-4
2C-T-22[53] File:2CT22 structure.png 648957-48-6
2C-T-23[53] File:2CT23 structure.png
2C-T-24[53] File:2CT24 structure.png
2C-T-25[53] File:2CT25 structure.png
2C-T-27[53] File:2CT27 structure.png 648957-52-2
2C-T-28[53] File:2CT28 structure.png 648957-54-4
2C-T-30[53] File:2CT30 structure.png
2C-T-31[53] File:2CT31 structure.png
2C-T-32[53] File:2CT32 structure.png
2C-T-33[53] File:2CT33 structure.png
2C-T-DFM H SCF2H File:2C-T-DFM structure.png
CYB210010 (2C-T-TFM)[55] H SCF3 File:CYB210010 structure.png
2C-T-DFP H SCH2CH2CF2H File:2C-T-DFP structure.png
2C-T-PARGY H SCH2C≡CH File:2C-T-PARGY structure.png
2C-DFM [4]Template:Rp H CHF2 File:2C-DFM.svg
2C-TFM H CF3 File:2C-TFM-Chemdraw.png 159277-08-4
2C-TFE H CH2CF3 File:2C-TFE structure.png
2C-PFE H CF2CF3 File:2C-PFE structure.png
2C-PFS H SF5 File:2C-PFS structure.png
2C-YN H C≡CH File:2C-YN skeletal.svg 752982-24-4
2C-V H CH=CH2 File:2C-V structure.png
2C-AL[56] H CH2CH=CH2 File:2C-AL structure.png

Related compounds

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Template:Sticky

Name Chemical name Structure Ref
N-Methyl-2C-I N-Methyl-4-iodo-2,5-dimethoxyphenethylamine File:N-Methyl-2C-I.svg
β-Methyl-2C-B 4-Bromo-2,5-dimethoxy-β-methylphenylethylamine File:BMB structure.png
β-Keto-2C-B (βk-2C-B) 4-Bromo-2,5-dimethoxy-β-ketophenylethylamine File:Βk-2C-B-skeletal.svg
25D-NM-NDEAOP (25D-NM-NDEPA) N-Methyl-N-(3-diethylamino-3-oxopropyl)-2,5-dimethoxy-4-methylphenethylamine File:25D-NM-NDEAOP.svg
25B-NAcPip N-(Piperidin-1-ylcarbonylmethyl)-4-bromo-2,5-dimethoxyphenethylamine File:25B-NAcPip structure.png
XOB N-[(4-Phenylbutoxy)hexyl]-4-bromo-2,5-dimethoxyphenethylamine File:XOB.svg [57]
TCB-2 [(7R)-3-Bromo-2,5-dimethoxy-bicyclo[4.2.0]octa-1,3,5-trien-7-yl]methanamine File:TCB-2.png
2CB-Ind (5-Bromo-4,7-dimethoxy-2,3-dihydro-1H-inden-1-yl)methanamine File:2CB-Indane.png
ZC-B 3-(4-Bromo-2,5-dimethoxyphenyl)azetidine File:WO2021-0137908-1 structure.png
DOM-CR (DOM-THIQ, 2C-D-CR) 5,8-Dimethoxy-7-methyl-1,2,3,4-tetrahydroisoquinoline File:DOM-CR.svg
DOB-CR (DOB-THIQ, 2C-B-CR) 5,8-Dimethoxy-7-bromo-1,2,3,4-tetrahydroisoquinoline File:DOB-CR.svg
N-Methyl-DOM-CR (Beatrice-CR, N-methyl-2C-D-CR) 2,7-Dimethyl-5,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline File:N-Methyl-DOM-CR.svg
LPH-5 (S)-3-(2,5-Dimethoxy-4-(trifluoromethyl)phenyl)piperidine File:LPH-5.svg
DEMPDHPCA-2C-D ("compound 45") 1-Methyl-3-(1-oxo-1-diethylaminomethyl)-5-(2,5-dimethoxy-4-methylphenyl)-3,6-dihydro-2H-pyridine File:DEMPDHPCA-2C-D.svg [58]
2C-B-morpholine 2-(4-Bromo-2,5-dimethoxyphenyl)morpholine File:2CB-norphenmetrazine structure.png [59][60]
2C-B-aminorex 5-(4-Bromo-2,5-dimethoxyphenyl)-4,5-dihydro-1,3-oxazol-2-amine File:2CB-AR structure.png
2C-B-PP 1-(2,5-Dimethoxy-4-bromophenyl)piperazine File:2C-B-PP Structure.svg
2C-B-BZP 1-[(4-Bromo-2,5-dimethoxyphenyl)methyl]piperazine File:2C-B-BZP.svg

See also

References

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  55. ↑ 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. Script error: No such module "CS1 identifiers". Template:Catalog lookup link
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