2C-H
Template:Cs1 config Template:Short description <templatestyles src="Infobox drug/styles.css"/> Script error: No such module "Infobox".Template:Template otherScript error: No such module "TemplatePar".{{Infobox drug/maintenance categoriesTemplate:Yesno | drug_name = | INN = | _drugtype =
| _has_physiological_data= | _has_gene_therapy=
| vaccine_type= | mab_type= | _number_of_combo_chemicals=Script error: No such module "ParameterCount". | _vaccine_data= | _mab_data= | _mab_vaccine_data= | _mab_other_data=101512COC1=CC(=C(C=C1)OC)CCN1S/C10H15NO2/c1-12-9-3-4-10(13-2)8(7-9)5-6-11/h3-4,7H,5-6,11H2,1-2H3WNCUVUUEJZEATP-UHFFFAOYSA-NTemplate:StdinchiciteTemplate:Stdinchicite138139 | _combo_data= | _physiological_data= | _clinical_data=
| _legal_data=
| _other_data=2-(2,5-dimethoxyphenyl)ethanamine
| _image_0_or_2 = 2C-H-Chemdraw.png2C-H-3d-sticks.png | _image_LR =
| _datapage = 2C-H (data page) | _vaccine_target=_type_not_vaccine | _legal_all= | _ATC_prefix_supplemental= | _has_EMA_link = | CAS_number=3600-86-0 | PubChem=76632 | ChemSpiderID=69096 | ChEBI=125507 | ChEMBL=287047 | DrugBank= | KEGG= | _hasInChI_or_Key=yes | UNII=9A8XF4GA0X | _hasJmol02 = |_hasMultipleCASnumbers = |_hasMultiplePubChemCIDs = |_hasMultipleChEBIs =
| _countSecondIDs=Script error: No such module "ParameterCount". | _countIndexlabels=Script error: No such module "ParameterCount". | _trackListSortletter= |QID = |QID2 = |Verifiedfields=verified |Watchedfields=verified |verifiedrevid=477216234}}
2C-H, also known as 2,5-dimethoxyphenethylamine (2,5-DMPEA), is a lesser-known drug of the phenethylamine and 2C (4-substituted 2,5-dimethoxyphenethylamine) families. It is the parent compound of the 2C drugs.
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 the book PiHKAL, Alexander Shulgin lists both the dosage and duration of 2C-H effects as unknown.[1] Very little data exists about the pharmacological properties, metabolism, and toxicity of 2C-H.
Pharmacology
| 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
2C-H is used as a precursor in the synthesis of other phenethylamines such as 2C-B, 2C-I, and 2C-N.[1]
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.[19]
Legal status
Canada
As of October 31, 2016; 2C-H is a controlled substance (Schedule III) in Canada.[20]
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.[21] 2C-H's DEA Drug Code is 7517.
See also
References
<templatestyles src="Reflist/styles.css" />
- ↑ a b c Script error: No such module "citation/CS1". 2C-H Entry in PiHKAL
- ↑ Script error: No such module "citation/CS1".
- ↑ Script error: No such module "citation/CS1".
- ↑ a b c Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ a b c Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ a b Script error: No such module "Citation/CS1".
- ↑ a b c Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "citation/CS1".
- ↑ a b Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "citation/CS1".
- ↑ Script error: No such module "citation/CS1".
Script error: No such module "Check for unknown parameters".
External links
- 2C-H - Isomer Design
- 2C-H - PiHKAL - Erowid
- 2C-H - PiHKAL - Isomer Design
- NIST WebBook Entry
- DEA's Microgram
Template:Psychedelics Template:Serotonin receptor modulators Template:TAAR modulators Template:Monoamine metabolism modulators Script error: No such module "Navbox". Template:Chemical classes of psychoactive drugs