:2C-H
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Infobox drug
| Verifiedfields = verified
| Watchedfields = verified
| verifiedrevid = 477216234
| drug_name =
| image = 2C-H-Chemdraw.png
| width = 175px
| caption =
| image2 = 2C-H-3d-sticks.png
| width2 = 175px
| pronounce =
| tradename =
| Drugs.com =
| MedlinePlus =
| licence_CA =
| licence_EU =
| DailyMedID =
| licence_US =
| pregnancy_AU =
| pregnancy_category =
| dependency_liability =
| addiction_liability =
| routes_of_administration =
| class =
| ATC_prefix =
| ATC_suffix =
| legal_status =
| bioavailability =
| protein_bound =
| metabolism =
| metabolites =
| onset =
| elimination_half-life =
| duration_of_action =
| excretion =
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 3600-86-0
| CAS_supplemental =
3166-74-3 (hydrochloride)
| PubChem = 76632
| IUPHAR_ligand =
| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 69096
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 9A8XF4GA0X
| KEGG =
| ChEBI = 125507
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 287047
| NIAID_ChemDB =
| PDB_ligand =
| synonyms = 2,5-Dimethoxyphenethylamine; 2,5-DMPEA
| IUPAC_name = 2-(2,5-dimethoxyphenyl)ethanamine
| C=10 | H=15 | N=1 | O=2
| SMILES = COC1=CC(=C(C=C1)OC)CCN
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C10H15NO2/c1-12-9-3-4-10(13-2)8(7-9)5-6-11/h3-4,7H,5-6,11H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WNCUVUUEJZEATP-UHFFFAOYSA-N
| melting_point = 138
| melting_high = 139
| melting_notes = (hydrochloride)
}}
2C-H, also known as 2,5-dimethoxyphenethylamine (2,5-DMPEA), is a lesser-known drug 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.{{CitePiHKAL}} [https://www.erowid.org/library/books_online/pihkal/pihkal032.shtml 2C-H Entry in PiHKAL] In the book PiHKAL, 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 of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors, albeit with far lower potency than other 2C drugs. It also shows affinity for the serotonin 5-HT1A receptor, higher than that of any other 2C drug. The drug exhibits agonist activity in vitro at the human trace amine associated receptor 1 (TAAR1).{{cite web|title="PubChem"|url=https://pubchem.ncbi.nlm.nih.gov/compound/76632#section=BioAssay-Results}}
2C-H produces visual and auditory changes in rodents, but is much less potent than other 2C drugs.{{cite journal | vauthors = Tirri M, Bilel S, Arfè R, Corli G, Marchetti B, Bernardi T, Boccuto F, Serpelloni G, Botrè F, De-Giorgio F, Golembiowska K, Marti M | title = Effect of -NBOMe Compounds on Sensorimotor, Motor, and Prepulse Inhibition Responses in Mice in Comparison With the 2C Analogs and Lysergic Acid Diethylamide: From Preclinical Evidence to Forensic Implication in Driving Under the Influence of Drugs | journal = Front Psychiatry | volume = 13 | issue = | pages = 875722 | date = 2022 | pmid = 35530025 | pmc = 9069068 | doi = 10.3389/fpsyt.2022.875722 | doi-access = free | url = }} 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 effects.{{cite journal | vauthors = Nichols CD | title = Psychedelics as potent anti-inflammatory therapeutics | journal = Neuropharmacology | volume = 219 | issue = | pages = 109232 | date = November 2022 | pmid = 36007854 | doi = 10.1016/j.neuropharm.2022.109232 | url = | doi-access = free }}{{cite book | vauthors = Flanagan TW, Nichols CD | title = Disruptive Psychopharmacology | chapter = Psychedelics and Anti-inflammatory Activity in Animal Models | series = Curr Top Behav Neurosci | volume = 56 | pages = 229–245 | date = 2022 | pmid = 35546383 | doi = 10.1007/7854_2022_367 | isbn = 978-3-031-12183-8 | chapter-url = }}{{cite journal | vauthors = Flanagan TW, Billac GB, Landry AN, Sebastian MN, Cormier SA, Nichols CD | title = Structure-Activity Relationship Analysis of Psychedelics in a Rat Model of Asthma Reveals the Anti-Inflammatory Pharmacophore | journal = ACS Pharmacol Transl Sci | volume = 4 | issue = 2 | pages = 488–502 | date = April 2021 | pmid = 33860179 | pmc = 8033619 | doi = 10.1021/acsptsci.0c00063 | url = }}
Chemistry
2C-H is used as a precursor in the synthesis of other phenethylamines such as 2C-B, 2C-I, and 2C-N.
The N-methyl derivative of 2C-H, N-methyl-2C-H, has reduced activational potency and efficacy at the serotonin 5-HT2A receptor compared to 2C-H.
History
2C-H was first synthesized in 1932 by Johannes S. Buck.{{cite journal| vauthors = Buck JS |title=Hydroxy- and Dihydroxyphenylethylmethylamines and their Ether|journal=Journal of the Chemical Society|date=1932|volume=54|issue=9|pages=3661–3665|doi=10.1021/ja01348a024}}
Legal status
=Canada=
As of October 31, 2016; 2C-H is a controlled substance (Schedule III) in Canada.{{Cite web|url=http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php|title=Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)|date=4 May 2016}}
= 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.{{cite web |title=Rules - 2013 - Establishment of Drug Codes for 26 Substances (SDAPA) |url= http://www.deadiversion.usdoj.gov/fed_regs/rules/2013/fr0104.htm |publisher=U.S. Department of Justice |access-date=22 July 2012|archive-date= 22 March 2015 |archive-url= https://web.archive.org/web/20150322225248/http://www.deadiversion.usdoj.gov/fed_regs/rules/2013/fr0104.htm |url-status=dead}} 2C-H's DEA Drug Code is 7517.
See also
References
{{Reflist}}
External links
- [https://isomerdesign.com/pihkal/explore/32 2C-H - Isomer Design]
- [https://erowid.org/library/books_online/pihkal/pihkal032.shtml 2C-H - PiHKAL - Erowid]
- [https://isomerdesign.com/pihkal/read/pk/32 2C-H - PiHKAL - Isomer Design]
- [http://webbook.nist.gov/cgi/cbook.cgi?ID=3600-86-0&Units=SI&cMS=onNIST%20WebBook NIST WebBook Entry]
- [https://web.archive.org/web/20081007020834/http://www.usdoj.gov/dea/programs/forensicsci/microgram/mg0808/mg0808.html DEA's Microgram]
{{Psychedelics}}
{{Serotonin receptor modulators}}
{{TAAR modulators}}
{{Monoamine metabolism modulators}}
{{Phenethylamines}}
{{Chemical classes of psychoactive drugs}}
{{DEFAULTSORT:2c-H}}
Category:2,5-Dimethoxyphenethylamines
Category:Alpha-1 adrenergic receptor agonists