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Revision as of 13:08, 24 February 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,071 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL.← Previous edit		Latest revision as of 20:33, 10 March 2024 edit undoInternetArchiveBot (talk | contribs)Bots, Pending changes reviewers5,388,266 edits Rescuing 1 sources and tagging 0 as dead.) #IABot (v2.0.9.5) (Maxim Masiutin - 17955
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			{{Short description|Chemical compound}}
	{{Drugbox		{{Drugbox
	| verifiedrevid = 400290854		| verifiedrevid = 415683864
	| IUPAC_name = 2-(7-methoxy-1,3-benzodioxol-5-yl)ethanamine		| IUPAC_name = 2-(7-Methoxy-1,3-benzodioxol-5-yl)ethanamine
	| image = Lophophine.png		| image = Lophophine.png
	| InChI = 1/C10H13NO3/c1-12-8-4-7(2-3-11)5-9-10(8)14-6-13-9/h4-5H,2-3,6,11H2,1H3
			<!--Clinical data-->
	| InChIKey = ORXQUAPZHKCCAX-UHFFFAOYAH
			| tradename =
		⚫	| pregnancy_category =
		⚫	| legal_status = Uncontrolled <small>(but may be covered under the ] in the ] and under similar bills in other countries due to its similarity to ] and ])</small>
		⚫	| routes_of_administration = ]
			<!--Pharmacokinetic data-->
		⚫	| bioavailability =
		⚫	| metabolism =
		⚫	| elimination_half-life =
		⚫	| excretion =
			<!--Identifiers-->
			| CAS_number_Ref = {{cascite|correct|??}}
		⚫	| CAS_number = 23693-38-1
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = C68IB79RC2
		⚫	| ATC_prefix = none
		⚫	| ATC_suffix =
		⚫	| PubChem = 90239
		⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
		⚫	| ChemSpiderID = 81465
			| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 159620		| ChEMBL = 159620
			<!--Chemical data-->
		⚫	| C=10 | H=13 | N=1 | O=3
		⚫	| smiles = O1c2cc(cc(OC)c2OC1)CCN
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C10H13NO3/c1-12-8-4-7(2-3-11)5-9-10(8)14-6-13-9/h4-5H,2-3,6,11H2,1H3		| StdInChI = 1S/C10H13NO3/c1-12-8-4-7(2-3-11)5-9-10(8)14-6-13-9/h4-5H,2-3,6,11H2,1H3
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = ORXQUAPZHKCCAX-UHFFFAOYSA-N		| StdInChIKey = ORXQUAPZHKCCAX-UHFFFAOYSA-N
⚫	| CAS_number = 23693-38-1
⚫	| ATC_prefix = none
⚫	| ATC_suffix =
⚫	| PubChem = 90239
⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫	| ChemSpiderID = 81465
⚫	| C = 10 | H = 13 | N = 1 | O = 3
	| molecular_weight = 195.22 g/mol
⚫	| smiles = O1c2cc(cc(OC)c2OC1)CCN
⚫	| bioavailability =
⚫	| metabolism =
⚫	| elimination_half-life =
⚫	| excretion =
⚫	| pregnancy_category = ?
⚫	| legal_status = Uncontrolled <small>(but may be covered under the ] in the ] and under similar bills in other countries due to its similarity to ] and ])</small>
⚫	| routes_of_administration = ]
	}}		}}
	'''Lophophine''', also known as '''3-methoxy-4,5-methylenedioxyphenethylamine''' ('''MMDPEA'''; '''5-Methoxy-MDPEA'''), is a ] and ] ] of the ] class. It is the ]-] ] of ], and is also closely related to ].		'''Lophophine''' ('''MMDPEA''' or '''3-methoxy-4,5-methylenedioxyphenethylamine''') is a putative ] and ] ] of the ] class. It is the ]-] ] of ], and is also closely related to ].
	] previously suggested that lophophine may be a ] of ] due to it being the only logical ] for the ] of several ]s known to be present in the ]. Subsequently, it was indeed shown to be a minor component of both Peyote and ].<ref name="pmid18720674">{{cite journal | author = Bruhn JG, El-Seedi HR, Stephanson N, Beck O, Shulgin AT | title = Ecstasy analogues found in cacti | journal = ] | volume = 40 | issue = 2 | pages = 219–22 | year = 2008 | month = June | pmid = 18720674 | doi = | url = }}</ref>		] originally suggested that lophophine may be a ] of ] (''Lophophora williamsii'') due to it being the only logical ] for the ] of several ]s known to be present in this cactus species.<ref name = Shul>{{Cite book | author = A. Shulgin and A. Shulgin | date = 1991 | title = Pihkal | pages = 701–702 | publisher = Transform Press | location = Berkeley}}</ref> Subsequently, lophophine was indeed shown to be a minor component of both peyote and ].<ref name="pmid18720674">{{cite journal |vauthors=Bruhn JG, El-Seedi HR, Stephanson N, Beck O, Shulgin AT | title = Ecstasy analogues found in cacti | journal = ] | volume = 40 | issue = 2 | pages = 219–22 |date=June 2008 | pmid = 18720674 | doi = 10.1080/02791072.2008.10400635| citeseerx = 10.1.1.689.4014 | s2cid = 11251286 }}</ref>
	Shulgin reports that lophophine is ] in the ] range of 150-250&nbsp;mg. He states that at these doses, MMDPEA is very similar to mescaline in action, and that a peaceful elevation of ], ], enhancement of ] ], and the generation of ] ] are all present. At dosages above 300&nbsp;mg, ]s that resemble those of standard doses of mescaline are said to begin to appear. Shulgin also notes that in contrast to mescaline, lophophine causes little ] or ].		Shulgin reports that lophophine is active in the ] range of 150–250&nbsp;mg. He states that at these doses, lophophine has some similarity to mescaline in action, in producing a peaceful elevation of ], ], and mild enhancement of ] ], but without the generation of ] ]. Shulgin also notes that (in contrast to mescaline), lophophine causes no ].<ref name = Shul/>
	== See also ==		== See also ==
	* ]
	* ]
	* ]		* ]
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	== External links ==		== External links ==
	*		*
		⚫	* {{Webarchive|url=https://web.archive.org/web/20140216210730/http://leda.lycaeum.org/?ID=16291 |date=2014-02-16 }}
	*
⚫	*
		⚫	{{Hallucinogens}}
	{{Entactogens}}		{{Entactogens}}
			{{Monoamine releasing agents}}
⚫	{{Hallucinogens}}
			{{Serotonin receptor modulators}}
	{{Serotonergics}}
	{{Phenethylamines}}		{{Phenethylamines}}
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	]		]
	]		]
			]