2C-H

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

2C-H
Names
Preferred IUPAC name
2-(2,5-Dimethoxyphenyl)ethan-1-amine
Other names
2,5-Dimethoxy-phenethylamine
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.153.556
PubChem CID
UNII
InChI
  • InChI=1S/C10H15NO2/c1-12-9-3-4-10(13-2)8(7-9)5-6-11/h3-4,7H,5-6,11H2,1-2H3 Y
    Key: WNCUVUUEJZEATP-UHFFFAOYSA-N Y
  • InChI=1/C10H15NO2/c1-12-9-3-4-10(13-2)8(7-9)5-6-11/h3-4,7H,5-6,11H2,1-2H3
    Key: WNCUVUUEJZEATP-UHFFFAOYAJ
SMILES
  • O(c1ccc(OC)cc1CCN)C
Properties
Chemical formula
 C10H15NO2
Molar mass 181.23 g/mol
Melting point 138 to 139 °C (280 to 282 °F; 411 to 412 K) (hydrochloride)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

History

2C-H was first synthesized in 1932 by Johannes S. Buck.[1]

Use

2C-H is used as a precursor in the synthesis of other substituted phenethylamines such as 2C-B, 2C-I, and 2C-N.[2] 2C-H has been found in trace amounts by the DEA's south central laboratory in tablets that were suspected of containing MDMA.

Pharmacology

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.[2] In the book PiHKAL, Alexander Shulgin lists both the dosage and duration of 2C-H effects as unknown.[2] Very little data exists about the pharmacological properties, metabolism, and toxicity of 2C-H.

Research

2C-H exhibits agonist activity in vitro at human trace amine associated receptor 1 expressed in RD-HGA16 CHO-K1 cells coexpressed with Galpha16 protein assessed as internal calcium mobilization.[3] 2C-H was found to be inactive in NCI In Vivo Anticancer Drug Screens for tumor model L1210 Leukemia.[3] It was found to be an active Alpha-1 adrenergic receptor agonist in rabbit ear arteries.[3] It has binding affinity towards 5-HT2C and 5-HT2A receptors in rats.[3] It features competitive antagonist activity at 5-HT serotonin receptor in Sprague-Dawley rat stomachs.[3] It exhibits binding affinity against rat 5-hydroxytryptamine 2C receptors using [3H]mesulergine as a radioligand.[3]

Canada

As of October 31, 2016; 2C-H is a controlled substance (Schedule III) in Canada.[4]

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.[5] 2C-H's DEA Drug Code is 7517.

See also

References
  1. Buck, Johannes S. (1932). "Hydroxy- and Dihydroxyphenylethylmethylamines and their Ether". Journal of the Chemical Society. 54 (9): 3661–3665. doi:10.1021/ja01348a024.
  2. Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. 2C-H Entry in PiHKAL
  3. ""PubChem"".
  4. "Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". 4 May 2016.
  5. Portman. "Rules - 2013 - Establishment of Drug Codes for 26 Substances (SDAPA)". usdoj. Retrieved 22 July 2012.
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