| Revision as of 17:55, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 455601329 of page 3-Methoxyamphetamine for the Chem/Drugbox validation project (updated: 'CAS_number'). |
Latest revision as of 20:20, 23 September 2024 edit JWBE (talk | contribs)Extended confirmed users10,126 edits removed Category:Phenol ethers; added Category:3-Methoxyphenyl compounds using HotCat |
| Line 1: |
Line 1: |
|
|
{{Short description|Stimulant drug of the amphetamine class}} |
|
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
|
|
{{Drugbox |
|
{{Drugbox |
|
|
| Verifiedfields = changed |
| ⚫ |
| verifiedrevid = 413268078 |
|
|
|
| Watchedfields = changed |
|
⚫ |
| verifiedrevid = 477219334 |
|
| IUPAC_name = 1-(3-methoxyphenyl)propan-2-amine |
|
| IUPAC_name = 1-(3-methoxyphenyl)propan-2-amine |
|
| image = 3-Methoxyamphetamine.png |
|
| image = 3-Methoxyamphetamine.png |
| Line 8: |
Line 10: |
|
| tradename = |
|
| tradename = |
|
| pregnancy_category = |
|
| pregnancy_category = |
|
| legal_status = ? |
|
| legal_status = |
|
| routes_of_administration = ] |
|
| routes_of_administration = ] |
|
|
|
|
| Line 15: |
Line 17: |
|
| metabolism = |
|
| metabolism = |
|
| elimination_half-life = |
|
| elimination_half-life = |
|
| excretion = |
|
| excretion = |
|
|
|
|
|
<!--Identifiers--> |
|
<!--Identifiers--> |
|
|
| CAS_number_Ref = {{cascite|correct|CAS}} |
|
| CAS_number = <!-- blanked - oldvalue: 17862-85-0 --> |
|
| CAS_number = 17862-85-0 |
|
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
|
| UNII = C2B7C98LY8 |
|
| ATC_prefix = none |
|
| ATC_prefix = none |
|
| ATC_suffix = |
|
| ATC_suffix = |
| Line 29: |
Line 34: |
|
<!--Chemical data--> |
|
<!--Chemical data--> |
|
| C=10 | H=15 | N=1 | O=1 |
|
| C=10 | H=15 | N=1 | O=1 |
|
⚫ |
| smiles = NC(C)CC1=CC=CC(OC)=C1 |
|
| molecular_weight = 165.232 g/mol |
|
| ⚫ |
| smiles = COc1cccc(c1)CC(N)C |
|
|
| InChI = 1/C10H15NO/c1-8(11)6-9-4-3-5-10(7-9)12-2/h3-5,7-8H,6,11H2,1-2H3 |
|
|
| InChIKey = VEJWNIYARKAHFI-UHFFFAOYAP |
|
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChI = 1S/C10H15NO/c1-8(11)6-9-4-3-5-10(7-9)12-2/h3-5,7-8H,6,11H2,1-2H3 |
|
| StdInChI = 1S/C10H15NO/c1-8(11)6-9-4-3-5-10(7-9)12-2/h3-5,7-8H,6,11H2,1-2H3 |
| Line 38: |
Line 40: |
|
| StdInChIKey = VEJWNIYARKAHFI-UHFFFAOYSA-N |
|
| StdInChIKey = VEJWNIYARKAHFI-UHFFFAOYSA-N |
|
}} |
|
}} |
|
|
|
|
|
'''''meta''-Methoxyamphetamine'''<ref>{{cite patent | country = GB | number = 1527479 | title = Acid Addition Salts of D-(+)-1-(3-Hydroxyphenyl)-2-Aminopropane and Their Manufacture and Use }}</ref> ('''MMA'''), also known as '''3-methoxyamphetamine''' ('''3-MA'''), is a ] ] from the ] family. It has similar effects in animal drug discrimination tests to the more widely known derivative ] (PMA),<ref>{{cite journal | vauthors = Glennon RA, Young R, Hauck AE | title = Structure-activity studies on methoxy-substituted phenylisopropylamines using drug discrimination methodology | journal = Pharmacology, Biochemistry, and Behavior | volume = 22 | issue = 5 | pages = 723–9 | date = May 1985 | pmid = 3839309 | doi = 10.1016/0091-3057(85)90520-9 | s2cid = 22341227 }}</ref> although with a slightly different ratio of monoamine release, being a combined ], ], and ] ] rather than a fairly ] ] like PMA.<ref>{{cite journal | vauthors = Tseng LF, Menon MK, Loh HH | title = Comparative actions of monomethoxyamphetamines on the release and uptake of biogenic amines in brain tissue | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 197 | issue = 2 | pages = 263–71 | date = May 1976 | pmid = 1271280 | authorlink3 = Horace Loh }}</ref><ref>{{cite journal | vauthors = Menon MK, Tseng LF, Loh HH | title = Pharmacological evidence for the central serotonergic effects of monomethoxyamphetamines | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 197 | issue = 2 | pages = 272–9 | date = May 1976 | pmid = 946817 }}</ref> 3-Methoxyamphetamine has similarly appeared on the illicit market as a ] alternative to ], although far more rarely than its infamous ].<ref>{{cite journal | vauthors = Dal Cason TA | title = A re-examination of the mono-methoxy positional ring isomers of amphetamine, methamphetamine and phenyl-2-propanone | journal = Forensic Science International | volume = 119 | issue = 2 | pages = 168–94 | date = June 2001 | pmid = 11376983 | doi = 10.1016/S0379-0738(00)00425-4 }}</ref> It produces ], a ], as one of its major ]s.<ref>{{cite journal | vauthors = Midha KK, Cooper JK, Bailey K, Hubbard JW | title = The metabolism of 3-methoxyamphetamine in dog, monkey and man | journal = Xenobiotica; the Fate of Foreign Compounds in Biological Systems | volume = 11 | issue = 2 | pages = 137–46 | date = February 1981 | pmid = 6894510 | doi = 10.3109/00498258109045284 }}</ref> |
|
|
|
|
|
== See also == |
|
|
* ] (OMA) |
|
|
* ] (3-MA) |
|
|
* ] (3-FA) |
|
|
* ] (Norfenfluramine) |
|
|
* ] (MMA) |
|
|
* ] (MMMA) |
|
|
* ] (4-ETA) |
|
|
|
|
|
== References == |
|
|
{{Reflist}} |
|
|
|
|
|
{{Stimulants}} |
|
|
{{Phenethylamines}} |
|
|
|
|
|
{{DEFAULTSORT:Methoxyamphetamine, 3-}} |
|
|
] |
|
|
] |
|
|
] |