Editing 2C-D (section)

{{Infobox drug
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477216133
| drug_name = 
| image = 2C-D 2DACS.svg
| width = 200px
| caption = 
| image2 = 2C-D-3d-sticks.png
| width2 = 175px

<!-- Clinical data -->
| pronounce = 
| tradename = 
| Drugs.com = 
| MedlinePlus = 
| licence_CA = 
| licence_EU = 
| DailyMedID = 
| licence_US = 
| pregnancy_AU = 
| pregnancy_category = 
| dependency_liability = 
| addiction_liability = 
| routes_of_administration = [[Oral administration|Oral]]
| class = [[Serotonin]] [[5-HT2 receptor|5-HT<sub>2</sub> receptor]] [[agonist]]; [[Serotonergic psychedelic]]; [[Hallucinogen]]
| ATC_prefix = 
| ATC_suffix = 

<!-- Legal status -->
| legal_AU = 
| legal_BR = F2
| legal_CA = Schedule III
| legal_DE = Anlage I
| legal_US = Schedule I
| legal_status = 

<!-- Pharmacokinetic data -->
| bioavailability = 
| protein_bound = 
| metabolism = 
| metabolites = 
| onset = 
| elimination_half-life = 
| duration_of_action = 4–6 hours<ref name="Shulgin" />
| excretion = 

<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 24333-19-5
| CAS_supplemental = 
| PubChem = 135740
| PubChemSubstance = 
| IUPHAR_ligand = 
| DrugBank = 
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 119559
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7J43GY6ONS
| KEGG = 
| ChEBI = 
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 124049
| NIAID_ChemDB = 
| PDB_ligand = 
| synonyms = 2,5-Dimethoxy-4-methyl-phenethylamine; 4-Methyl-2,5-dimethoxyphenethylamine; 2C-M; LE-25; LE25

<!-- Chemical data -->
| IUPAC_name = 2-(2,5-dimethoxy-4-methylphenyl)ethan-1-amine
| C=11 | H=17 | N=1 | O=2 
| SMILES = O(c1cc(c(OC)cc1CCN)C)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C11H17NO2/c1-8-6-11(14-3)9(4-5-12)7-10(8)13-2/h6-7H,4-5,12H2,1-3H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = UNQQFDCVEMVQHM-UHFFFAOYSA-N

<!-- Physical data -->
| melting_point = 213
| melting_high = 214
| melting_notes = ([[hydrochloride]])
}}

'''2C-D''', also known as '''2C-M''' or as '''2,5-dimethoxy-4-methylphenethylamine''', is a [[Psychedelics, dissociatives and deliriants|psychedelic drug]] of the [[2C (psychedelics)|2C family]] that is sometimes used as an [[entheogen]]. It was first synthesized in 1970 by a team from the Texas Research Institute of Mental Sciences,<ref name="pmid5412084">{{cite journal |vauthors=Ho BT, Tansey LW, Balster RL, An R, McIsaac WM, Harris RT |title=Amphetamine analogs. II. Methylated phenethylamines |journal=Journal of Medicinal Chemistry |volume=13 |issue=1 |pages=134–5 |date=January 1970 |pmid=5412084 |doi= 10.1021/jm00295a034}}</ref> and its activity was subsequently investigated in humans by [[Alexander Shulgin]].