2C-H
Pharmaceutical compound
From Wikipedia, the free encyclopedia
2C-H, also known as 2,5-dimethoxyphenethylamine (2,5-DMPEA) or as DMPEA-4, is a chemical compound of the phenethylamine and 2C families.[1] It is the parent compound of the 2C drugs, which are also known as 4-substituted 2,5-dimethoxyphenethylamines.[1]
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| Other names | 2,5-Dimethoxyphenethylamine; 2,5-DMPEA; DMPEA-4; NCS-168525; 2C-DOH |
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| Pharmacokinetic data | |
| Onset of action | Unknown[1] |
| Duration of action | Unknown[1] |
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| ECHA InfoCard | 100.153.556 |
| Chemical and physical data | |
| Formula | C10H15NO2 |
| Molar mass | 181.235 g·mol−1 |
| 3D model (JSmol) | |
| Melting point | 138 to 139 °C (280 to 282 °F) (hydrochloride) |
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Use and effects
There is no record of 2C-H trials in humans, as it would likely be destroyed by monoamine oxidase enzymes before causing any significant psychoactive effects.[1] In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists both the dose and duration of 2C-H effects as unknown.[1]
Pharmacology
Pharmacodynamics
| Target | Affinity (Ki, nM) |
|---|---|
| 5-HT1A | 70 |
| 5-HT1B | ND |
| 5-HT1D | ND |
| 5-HT1E | ND |
| 5-HT1F | ND |
| 5-HT2A | 1,600–3,000 (Ki) 2,408–>10,000 (EC50) 17,800 (IC50) 0–78% (Emax) |
| 5-HT2B | 6,200 (EC50) 46% (Emax) |
| 5-HT2C | 4,100–5,520 (Ki) 1,175–3,967 (EC50) 76% (Emax) |
| 5-HT3 | ND |
| 5-HT4 | ND |
| 5-HT5A | ND |
| 5-HT6 | ND |
| 5-HT7 | ND |
| α1A | 7,900 (Ki) 11,000 (EC50) |
| α1B, α1D | ND |
| α2A | 1,000 |
| α2B, α2C | ND |
| β1–β3 | ND |
| D1 | >14,000 |
| D2 | 9,000 |
| D3 | >17,000 |
| D4, D5 | ND |
| H1 | >25,000 |
| TAAR1 | 11,000 (Ki) (mouse) 900 (Ki) (rat) 7,500 (EC50) (mouse) 1,500 (EC50) (rat) 2,010–6,500 (EC50) (human) 56% (Emax) (mouse) 80% (Emax) (rat) 53–69% (Emax) (human) |
| SERT | >30,000 (Ki) 311,000 (IC50) ND (EC50) |
| NET | >30,000 (Ki) 125,000 (IC50) ND (EC50) |
| DAT | >30,000 (Ki) 857,000 (IC50) ND (EC50) |
| MAO-A | ND (IC50) |
| MAO-B | 1,700 (IC50) |
| Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [2][3][4][5][6][7][8][9][10][11][12][13][14] | |
2C-H acts as a partial agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors, albeit with far lower potency than other 2C drugs.[4][6][8][9] It also shows affinity for the serotonin 5-HT1A receptor, higher than that of any other 2C drug.[4] The drug exhibits agonist activity in vitro at the human trace amine associated receptor 1 (TAAR1).[15]
2C-H produces visual and auditory changes in rodents, but is much less potent than other 2C drugs.[16] It also produces hypolocomotion at high doses similarly to other psychedelics, but failed to affect prepulse inhibition in contrast to other psychedelics.[16] The drug shows highly potent and fully efficacious anti-inflammatory effects.[17][18][9]
Chemistry
Synthesis
The chemical synthesis of 2C-H has been described.[1][19] It is used as a precursor in the synthesis of other phenethylamines such as 2C-B, 2C-I, and 2C-N.[1]
Analogues and derivatives
2C-H (2,5-DMPEA) is one of several possible positional isomers of dimethoxyphenethylamine (DMPEA).[19]
2C-H is the parent compound of the 2C series of psychedelic drugs, also known as 4-substituted 2,5-dimethoxyphenethylamines.[1][19] These drugs include 2C-B, 2C-C, 2C-D, 2C-E, and 2C-I, among others.[1][19]
The N-methyl derivative of 2C-H, N-methyl-2C-H, has reduced activational potency and efficacy at the serotonin 5-HT2A receptor compared to 2C-H.[6]
History
2C-H was first synthesized in 1932 by Johannes S. Buck.[20]
Society and culture
Legal status
Canada
As of October 31, 2016; 2C-H is a controlled substance (Schedule III) in Canada.[21]
United States
As of July 9, 2012, 2C-H is a Schedule I controlled substance in the United States, under the Synthetic Drug Abuse Prevention Act of 2012.[22] 2C-H's DEA Drug Code is 7517.