2C-H

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2C-H
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Names
Preferred IUPAC name
2-(2,5-Dimethoxyphenyl)ethan-1-amine
Other names
2,5-Dimethoxy-phenethylamine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
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PubChem CID
UNII
  • 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 Yes check.svgY
    Key: WNCUVUUEJZEATP-UHFFFAOYSA-N Yes check.svgY
  • 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
  • O(c1ccc(OC)cc1CCN)C
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).
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Infobox references

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

Contents

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.[ 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 , 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

Related Research Articles

2C-T-21 Chemical compound

2C-T-21 is a psychedelic phenethylamine of the 2C family sometimes used as an entheogen. It was first synthesized by Alexander Shulgin.

2,5-Dimethoxy-4-methylamphetamine Chemical compound

2,5-Dimethoxy-4-methylamphetamine is a psychedelic and a substituted amphetamine. It was first synthesized by Alexander Shulgin, and later reported in his book PiHKAL: A Chemical Love Story. DOM is classified as a Schedule I substance in the United States, and is similarly controlled in other parts of the world. Internationally, it is a Schedule I drug under the Convention on Psychotropic Substances. It is generally taken orally.

2,5-Dimethoxy-4-bromoamphetamine Chemical compound

Dimethoxybromoamphetamine (DOB), also known as brolamfetamine (INN) and bromo-DMA, is a psychedelic drug and substituted amphetamine of the phenethylamine class of compounds. DOB was first synthesized by Alexander Shulgin in 1967. Its synthesis and effects are documented in Shulgin's book PiHKAL: A Chemical Love Story.

3,4-Methylenedioxyamphetamine Empathogen-entactogen, psychostimulant, and psychedelic drug of the amphetamine family

3,4-Methylene​dioxy​amphetamine (MDA), known commonly as sass, is an empathogen-entactogen, psychostimulant, and psychedelic drug of the amphetamine family that is encountered mainly as a recreational drug. In terms of pharmacology, MDA acts most importantly as a serotonin-norepinephrine-dopamine releasing agent (SNDRA). In most countries, the drug is a controlled substance and its possession and sale are illegal.

2C-T-4 Chemical compound

2C-T-4 (2,5-dimethoxy-4-isopropylthiophenethylamine) is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin and is used as entheogenic recreational drug.

2,5-Dimethoxy-4-chloroamphetamine

2,5-Dimethoxy-4-chloroamphetamine (DOC) is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was presumably first synthesized by Alexander Shulgin, and was described in his book PiHKAL.

2C-T Chemical compound

2C-T is a psychedelic and hallucinogenic drug of the 2C family. It is used by some as an entheogen. It has structural and pharmacodynamic properties similar to the drugs mescaline and 2C-T-2.

2C-TFM Chemical compound

2C-TFM is a psychedelic phenethylamine of the 2C family. It was first synthesized in the laboratory of David E. Nichols. It has also been called 2C-CF3, a name derived from the Para-trifluoromethyl group it contains.

2,5-Dimethoxy-4-ethylamphetamine

2,5-Dimethoxy-4-ethylamphetamine is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized by Alexander Shulgin, and was described in his book PiHKAL.

2C-T-15 Chemical compound

2C-T-15 or 2,5-dimethoxy-4-(β-cyclopropylthio)phenethylamine is a psychedelic phenethylamine of the 2C family. It was presumably first synthesized by Alexander Shulgin and reported in his book PiHKAL .

2C-T-17 Chemical compound

2C-T-17 or 2,5-dimethoxy-4-(β-secbutylthio)phenethylamine is a psychedelic phenethylamine of the 2C family. It was presumably first synthesized by Alexander Shulgin and reported in his book PiHKAL .

2,5-Dimethoxy-4-butylamphetamine Chemical compound

2,5-Dimethoxy-4-butylamphetamine (DOBU) is a lesser-known psychedelic drug and a substituted Amphetamine. DOBU was first synthesized by Alexander Shulgin. In his book PiHKAL (Phenethylamines i Have Known And Loved), only low dosages of 2–3 mg were tested, with the duration simply listed as "very long". DOBU produces paresthesia and difficulty sleeping, but with few other effects. Compared to shorter chain homologues such as DOM, DOET and DOPR which are all potent hallucinogens, DOBU has an even stronger 5-HT2 binding affinity but fails to substitute for hallucinogens in animals or produce hallucinogenic effects in humans, suggesting it has low efficacy and is thus an antagonist or weak partial agonist at the 5-HT2A receptor.

2,5-Dimethoxy-4-amylamphetamine Chemical compound

Dimethoxy-4-amylamphetamine (DOAM) is a lesser-known psychedelic drug and a substituted amphetamine. DOAM was first synthesized by Alexander Shulgin. In his book PiHKAL (Phenethylamines i Have Known And Loved), the minimum dosage is listed as 10 mg, and the duration is unknown. DOAM produces a bare threshold and tenseness. As the 4-alkyl chain length is increased from shorter homologues such as DOM, DOET, DOPR, and DOBU which are all potent hallucinogens, the 5-HT2 binding affinity increases, rising to a maximum with the 4-(n-hexyl) derivative before falling again with even longer chains, but compounds with chain length longer than n-propyl, or with other bulky groups such as isopropyl, t-butyl or γ-phenylpropyl at the 4- position, fail to substitute for hallucinogens in animals or produce hallucinogenic effects in humans, suggesting these have low efficacy and are thus antagonists or weak partial agonists at the 5-HT2A receptor.

2,5-Dimethoxy-4-ethoxyamphetamine Psychedelic drug

2,5-Dimethoxy-4-ethoxyamphetamine (MEM) is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized by Alexander Shulgin. In his book PiHKAL, he lists the active dose range as 20–50 mg, and the duration as 10–14 hours. According to Shulgin, MEM produces color enhancement, visual phenomena, and pattern movement, among other effects.

MMDA-2

MMDA-2 (2-methoxy-4,5-methylenedioxyamphetamine) is a psychedelic drug of the amphetamine class. It is closely related to MMDA and MDA.

2,5-Dimethoxy-4-fluoroamphetamine

2,5-Dimethoxy-4-fluoroamphetamine (DOF) is a psychedelic drug of the phenethylamine and amphetamine classes. Alexander Shulgin briefly describes DOF in his book PiHKAL:

Animal studies that have compared DOF to the highly potent DOI and DOB imply that the human activity will be some four to six times less than these two heavier halide analogues.

DO<em>x</em>

4-Substituted-2,5-dimethoxyamphetamines (DOx) is a chemical class of substituted amphetamine derivatives featuring methoxy groups at the 2- and 5- positions of the phenyl ring, and a substituent such as alkyl or halogen at the 4- position of the phenyl ring. Most compounds of this class are potent and long-lasting psychedelic drugs, and act as highly selective 5-HT2A, 5-HT2B, and 5-HT2C receptor partial agonists. A few bulkier derivatives such as DOAM have similarly high binding affinity for 5-HT2 receptors but instead act as antagonists, and so do not produce psychedelic effects though they retain amphetamine-like stimulant effects.

2C-T-16 Chemical compound

2C-T-16 is a lesser-known psychedelic drug. It was originally named by Alexander Shulgin as described in his book PiHKAL, however while Shulgin began synthesis of this compound he only got as far as the nitrostyrene intermediate, and did not complete the final synthetic step. Synthesis of 2C-T-16 was finally achieved by Daniel Trachsel some years later, and it was subsequently reported as showing similar psychedelic activity to related compounds, with a dose range of 10–25 mg and a duration of 4–6 hours, making it around the same potency as the better-known saturated analogue 2C-T-7, but with a significantly shorter duration of action. Binding studies in vitro showed 2C-T-16 to have a binding affinity of 44nM at 5-HT2A and 15nM at 5-HT2C. 2C-T-16 and related derivatives are potent partial agonists of the 5-HT1A, 5-HT2A, 5-HT2B and 5-HT2C receptors and induce a head-twitch response in mice.

2,5-Dimethoxy-4-isopropylamphetamine

2,5-Dimethoxy-4-isopropylamphetamine is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized by Alexander Shulgin, and was described in his book PiHKAL. Shulgin described DOiPR as being at least an order of magnitude weaker than DOPr, with doses of 20–30 mg required to produce valid changes in mental state. Very little data exists about the pharmacological properties, metabolism, and toxicity of DOiPR.

4C-B Chemical compound

4C-B is a lesser-known psychedelic drug which is related to 2C-B and DOB. It is a reasonably potent 5-HT2A receptor partial agonist with a Ki of 7.6nM, but has relatively low efficacy. It is briefly mentioned in Alexander Shulgin's book PiHKAL but was never tested by him, however it has subsequently been tested by other researchers and was found to be active in a dose range of 50-80mg with a duration of around 8 hours, though with generally milder effects than 2C-B or DOB.

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. 1 2 3 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. 1 2 3 4 5 6 ""PubChem"".
  4. http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php
  5. Portman. "Rules - 2013 - Establishment of Drug Codes for 26 Substances (SDAPA)". usdoj. Retrieved 22 July 2012.