2C-H

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2C-H
2C-H-Chemdraw.png
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Names
IUPAC name
2-(2,5-Dimethoxyphenyl)ethanamine
Other names
2,5-Dimethoxy-phenethylamine
Identifiers
  • 3600-86-0 (free base) ☒N
  • 3166-74-3 (HCl salt) ☒N
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL287047 ☑Y
ChemSpider
  • 69096 ☑Y
ECHA InfoCard 100.153.556
PubChem CID
  • 76632
UNII
  • 9A8XF4GA0X ☒N
Properties
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 ☑Y☒N ?)
Infobox references

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

History

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

Usage

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.[citation needed]

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 (Phenethylamines i Have Known And Loved), Alexander Shulgin lists both the dosage and duration of 2C-H effects as unknown.[3] Very little data exists about the pharmacological properties, metabolism, and toxicity of 2C-H.

Research

It exhibits agonist activity at human trace amine associated receptor 1 expressed in RD-HGA16 CHO-K1 cells coexpressed with Galpha16 protein assessed as internal calcium mobilization.[4] 2C-H was found to be inactive in NCI In Vivo Anticancer Drug Screens for tumor model L1210 Leukemia.[5] It was found to be an active Alpha-1 adrenergic receptor agonist in rabbit ear arteries.[6] It has binding affinity towards 5-HT2C and 5-HT2A receptors in rats.[7] It features competitive antagonist activity at 5-HT serotonin receptor in Sprague-Dawley rat stomachs.[8] It exhibits binding affinity against rat 5-hydroxytryptamine 2C receptors using [3H]mesulergine as a radioligand.[9]

Legal Status

Canada

As of October 31, 2016; 2C-H is a controlled substance (Schedule III) in Canada. http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php

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.[10] 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. ^ a b Shulgin, Alexander; Ann Shulgin (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
  3. ^ Shulgin, Alexander; Ann Shulgin (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
  4. ^ ""PubChem"".
  5. ^ ""PubChem"".
  6. ^ ""PubChem"".
  7. ^ ""PubChem"".
  8. ^ ""PubChem"".
  9. ^ ""PubChem"".
  10. ^ Portman. "Rules - 2013 - Establishment of Drug Codes for 26 Substances (SDAPA)". usdoj. Retrieved 22 July 2012.

External links

  • PubChem Entry
  • NIST WebBook Entry
  • 2C-H Entry in PiHKAL
  • 2C-H Entry in PiHKAL • info
  • DEA's Microgram
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