2C-H (2,5-dimethoxyphenethylamine) is a lesser-known
substituted phenethylamine
Substituted phenethylamines (or simply phenethylamines) are a chemical class of organic compounds that are based upon the phenethylamine structure; the class is composed of all the derivative compounds of phenethylamine which can be formed by ...
of the
2C family.
History
2C-H was first synthesized in 1932 by Johannes S. Buck.
Use
2C-H is used as a precursor in the synthesis of other
substituted phenethylamine
Substituted phenethylamines (or simply phenethylamines) are a chemical class of organic compounds that are based upon the phenethylamine structure; the class is composed of all the derivative compounds of phenethylamine which can be formed by ...
s such as
2C-B
2C-B (4-Bromo-2,5-dimethoxyphenethylamine) is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin in 1974. In Shulgin's book '' PiHKAL'', the dosage range is listed as 12–24 mg. As a recreational drug, 2C-B is so ...
,
2C-I
2C-I is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin and described in his 1991 book '' PiHKAL'' (''Phenethylamines I Have Known and Loved''). The drug has been used recreationally as psychedelic and ...
, and
2C-N.
2C-H has been found in trace amounts by the DEA's south central laboratory in tablets that were suspected of containing
MDMA
3,4-Methylenedioxymethamphetamine (MDMA), commonly seen in Tablet (pharmacy), tablet form (ecstasy) and crystal form (molly or mandy), is a potent empathogen–entactogen with stimulant properties primarily used for Recreational dru ...
.
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.
[2C-H Entry in ''PiHKAL'']
/ref> In the book '' PiHKAL'', Alexander Shulgin
Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American medicinal chemist, biochemist, organic chemist, pharmacologist, psychopharmacologist, and author. He is credited with introducing 3,4-methylenedioxymethamph ...
lists both the dosage and duration of 2C-H effects as unknown. Very little data exists about the pharmacological properties, metabolism, and toxicity of 2C-H.
Research
2C-H exhibits agonist
An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the ago ...
activity ''in vitro
''In vitro'' (meaning in glass, or ''in the glass'') studies are performed with microorganisms, cells, or biological molecules outside their normal biological context. Colloquially called "test-tube experiments", these studies in biology an ...
'' at human trace amine associated receptor 1
Trace amine-associated receptor 1 (TAAR1) is a trace amine-associated receptor (TAAR) protein that in humans is encoded by the ''TAAR1'' gene. TAAR1 is an intracellular amine-activated and G protein-coupled receptor (GPCR) that is primarily ex ...
expressed in RD-HGA16 CHO-K1 cells coexpressed with Galpha16 protein assessed as internal calcium mobilization. 2C-H was found to be inactive in NCI In Vivo Anticancer Drug Screens for tumor model L1210 Leukemia. It was found to be an active Alpha-1 adrenergic receptor
alpha-1 (α1) adrenergic receptors are G protein-coupled receptors (GPCRs) associated with the Gq heterotrimeric G protein. α1-adrenergic receptors are subdivided into three highly homologous subtypes, i.e., α1A-, α1B-, and α1D-adrenergic ...
agonist in rabbit ear arteries. It has binding affinity towards 5-HT2C
The 5-HT2C receptor is a subtype of 5-HT receptor that binds the endogenous neurotransmitter serotonin (5-hydroxytryptamine, 5-HT). It is a G protein-coupled receptor (GPCR) that is coupled to Gq/G11 and mediates excitatory neurotransmission. ...
and 5-HT2A
The 5-HT2A receptor is a subtype of the 5-HT2 receptor that belongs to the serotonin receptor family and is a G protein-coupled receptor (GPCR). The 5-HT2A receptor is a cell surface receptor, but has several intracellular locations. 5-HT is s ...
receptors in rats. It features competitive antagonist activity at 5-HT serotonin receptor in Sprague-Dawley rat stomachs. It exhibits binding affinity against rat 5-hydroxytryptamine 2C receptors using H esulergine as a radioligand.
Legal status
Canada
As of October 31, 2016; 2C-H is a controlled substance (Schedule III) in Canada.
United States
As of July 9, 2012, 2C-H is a Schedule I controlled substance
This is the list of Schedule I drugs as defined by the United States Controlled Substances Act. 21 CFRbr>1308.11(CSA Sched I) with changes through (Oct 18, 2012). Retrieved September 6, 2013. The following findings are required for drugs to be pl ...
in the United States
The United States of America (U.S.A. or USA), commonly known as the United States (U.S. or US) or America, is a country primarily located in North America. It consists of 50 states, a federal district, five major unincorporated territorie ...
, under the Synthetic Drug Abuse Prevention Act of 2012
The Food and Drug Administration Safety and Innovation Act of 2012 (FDASIA) is a piece of American regulatory legislation signed into law on July 9, 2012. It gives the United States Food and Drug Administration (FDA) the authority to collect user ...
. 2C-H's DEA Drug Code is 7517.
See also
* Phenethylamine
Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace amin ...
* 2C (psychedelics)
2C (2C-''x'') is a general name for the family of psychedelic drug, psychedelic phenethylamines containing Methoxy, methoxy groups on the 2 and 5 carbon, positions of a benzene ring. Most of these compounds also carry lipophilic substituents at the ...
* PiHKAL
* Psychedelics, dissociatives and deliriants
Hallucinogens are a large, diverse class of psychoactive drugs that can produce altered states of consciousness characterized by major alterations in thought, mood, and perception as well as other changes. Most hallucinogens can be categorized ...
References
External links
NIST WebBook Entry
{{DEFAULTSORT:2c-H
2C (psychedelics)