2C-H

Clinical data
Other names	2,5-Dimethoxyphenethylamine; 2,5-DMPEA; DMPEA-4; NCS-168525; 2C-DOH
ATC code	None
Pharmacokinetic data
Onset of action	Unknown[1]
Duration of action	Unknown[1]
Identifiers
IUPAC name 2-(2,5-dimethoxyphenyl)ethanamine
CAS Number	3600-86-0 Y 3166-74-3 (hydrochloride)
PubChemCID	76632
ChemSpider	69096 Y
UNII	9A8XF4GA0X
ChEBI	CHEBI:125507
ChEMBL	ChEMBL287047 Y
CompTox Dashboard(EPA)	DTXSID80189564
ECHA InfoCard	100.153.556
Chemical and physical data
Formula	C10H15NO2
Molar mass	181.235 g·mol−1
3D model (JSmol)	Interactive image
Melting point	138 to 139 °C (280 to 282 °F) (hydrochloride)
SMILES COC1=CC(=C(C=C1)OC)CCN
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
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2C-H, also known as2,5-dimethoxyphenethylamine (2,5-DMPEA) or asDMPEA-4, is achemical compound of thephenethylamine and2C families.^[1] It is theparent compound of the 2C drugs, which are also known as 4-substituted 2,5-dimethoxyphenethylamines.^[1]

There is no record of 2C-H trials in humans, as it would likely be destroyed bymonoamine oxidase enzymes before causing any significant psychoactive effects.^[1] In his bookPiHKAL (Phenethylamines I Have Known and Loved),Alexander Shulgin lists both the dose andduration of 2C-H effects as unknown.^[1]

2C-H acts as apartial agonist of theserotonin5-HT_2A,5-HT_2B, and5-HT_2C receptors, albeit with far lowerpotency than other 2C drugs.^[4][6][8][9] It also showsaffinity for the serotonin5-HT_1A receptor, higher than that of any other 2C drug.^[4] The drug exhibitsagonist activityin vitro at the humantrace amine associated receptor 1 (TAAR1).^[15]

2C-H producesvisual andauditory changes in rodents, but is much lesspotent than other 2C drugs.^[16] It also produceshypolocomotion at high doses similarly to other psychedelics, but failed to affectprepulse inhibition in contrast to other psychedelics.^[16] The drug shows highly potent and fully efficaciousanti-inflammatory effects.^[17][18][9]

Thechemical synthesis of 2C-H has been described.^[1][19] It is used as aprecursor in the synthesis of otherphenethylamines such as2C-B,2C-I, and2C-N.^[1]

2C-H (2,5-DMPEA) is one of several possiblepositional isomers ofdimethoxyphenethylamine (DMPEA).^[19]

2C-H is theparent compound of the2C series ofpsychedelic drugs, also known as 4-substituted 2,5-dimethoxyphenethylamines.^[1][19] These drugs include2C-B,2C-C,2C-D,2C-E, and2C-I, among others.^[1][19]

TheN-methylderivative of 2C-H,N-methyl-2C-H, has reducedactivationalpotency andefficacy at theserotonin5-HT_2A receptor compared to 2C-H.^[6]

2C-H was first synthesized in 1932 by Johannes S. Buck.^[20]

As of October 31, 2016; 2C-H is a controlled substance (Schedule III) in Canada.^[21]

As of July 9, 2012, 2C-H is aSchedule I controlled substance in theUnited States, under theSynthetic Drug Abuse Prevention Act of 2012.^[22] 2C-H's DEA Drug Code is 7517.

• Substituted methoxyphenethylamine
• 2C (psychedelics)

• 2C-H - Isomer Design
• 2C-H - PsychonautWiki
• 2C-H - PiHKAL - Erowid
• 2C-H - PiHKAL - Isomer Design
• 2C-H - The Shulgin Index

• Drugs not assigned an ATC code
• 2C (psychedelics)
• 5-HT2A agonists
• 5-HT2B agonists
• 5-HT2C agonists
• Alpha1-adrenergic agonists
• Anti-inflammatory agents
• Monoamine oxidase inhibitors
• PiHKAL
• TAAR1 agonists

• Articles with short description
• Short description is different from Wikidata
• ECHA InfoCard ID from Wikidata
• Chemical pages without DrugBank identifier
• Articles without KEGG source
• Drugs with no legal status