2C-H, also known as 2,5-dimethoxyphenethylamine (2,5-DMPEA), is a lesser-known

drug A drug is any chemical substance other than a nutrient or an essential dietary ingredient, which, when administered to a living organism, produces a biological effect. Consumption of drugs can be via insufflation (medicine), inhalation, drug i ...

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.2C-H Entry in ''PiHKAL''
/ref> In the book ''

PiHKAL ''PiHKAL: A Chemical Love Story'' is a book by Alexander Shulgin and Ann Shulgin published in 1991. The subject of the work is Psychoactive drug, psychoactive phenethylamine Derivative (chemistry), chemical derivatives, notably those that act ...

'', Alexander Shulgin 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.

Pharmacology

2C-H acts as a

partial agonist In pharmacology, partial agonists are drugs that bind to and activate a given Receptor (biochemistry), receptor, but have only partial Intrinsic activity, efficacy at the receptor relative to a full agonist. They may also be considered Ligand (bio ...

of the

serotonin Serotonin (), also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter with a wide range of functions in both the central nervous system (CNS) and also peripheral tissues. It is involved in mood, cognition, reward, learning, ...

5-HT_2A, 5-HT_2B, and 5-HT_2C receptors, albeit with far lower potency than other 2C drugs. It also shows

affinity Affinity may refer to: Commerce, finance and law * Affinity (law), kinship by marriage * Affinity analysis, a market research and business management technique * Affinity Credit Union, a Saskatchewan-based credit union * Affinity Equity Pa ...

for the serotonin 5-HT_1A receptor, higher than that of any other 2C drug. The drug exhibits

agonist An agonist is a chemical that activates a Receptor (biochemistry), receptor to produce a biological response. Receptors are Cell (biology), cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an R ...

activity ''

in vitro ''In vitro'' (meaning ''in glass'', or ''in the glass'') Research, studies are performed with Cell (biology), cells or biological molecules outside their normal biological context. Colloquially called "test-tube experiments", these studies in ...

'' at the human trace amine associated receptor 1 (TAAR1). 2C-H produces

visual The visual system is the physiological basis of visual perception (the ability to detect and process light). The system detects, transduces and interprets information concerning light within the visible range to construct an image and buil ...

and auditory changes in rodents, but is much less potent than other 2C drugs. It also produces hypolocomotion at high doses similarly to other psychedelics, but failed to affect prepulse inhibition in contrast to other psychedelics. The drug shows highly potent and fully efficacious

anti-inflammatory Anti-inflammatory is the property of a substance or treatment that reduces inflammation, fever or swelling. Anti-inflammatory drugs, also called anti-inflammatories, make up about half of analgesics. These drugs reduce pain by inhibiting mechan ...

effects.

Chemistry

2C-H is used as a precursor in the synthesis of other phenethylamines such as 2C-B,

2C-I 2C-I, also known as 2,5-dimethoxy-4-iodophenethylamine, is a phenethylamine of the 2C family with psychedelic effects. It was first synthesized by Alexander Shulgin, and is described in Shulgin's book ''PiHKAL'' (1991). The substance is con ...

, and

2C-N 2C-N, also known as 2,5-dimethoxy-4-nitrophenethylamine, is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin. Use Shulgin, in his book ''PiHKAL'', as well as other sources, list the dosage range as ...

. The ''N''-methyl

derivative In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...

of 2C-H, ''N''-methyl-2C-H, has reduced activational potency and

efficacy Efficacy is the ability to perform a task to a satisfactory or expected degree. The word comes from the same roots as '' effectiveness'', and it has often been used synonymously, although in pharmacology a distinction is now often made betwee ...

at the

5-HT_2A receptor compared to 2C-H.

History

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

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 in the

United States The United States of America (USA), also known as the United States (U.S.) or America, is a country primarily located in North America. It is a federal republic of 50 U.S. state, states and a federal capital district, Washington, D.C. The 48 ...

, under the Synthetic Drug Abuse Prevention Act of 2012. 2C-H's DEA Drug Code is 7517.

References

External links

2C-H - Isomer Design

2C-H - PiHKAL - Erowid

2C-H - PiHKAL - Isomer Design

NIST WebBook Entry

{{DEFAULTSORT:2c-H 2,5-Dimethoxyphenethylamines 2C (psychedelics) 5-HT2A agonists 5-HT2B agonists 5-HT2C agonists Alpha-1 adrenergic receptor agonists Monoamine oxidase inhibitors TAAR1 agonists