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Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'StdInChI', 'StdInChIKey', 'CAS_number').
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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| IUPAC_name = 2-(1,3-benzodioxol-5-yl)-2-methoxyethanamine
| Watchedfields = changed
| image = 3,4-methylenedioxy-beta-methoxy-phenethylamine.png
| drug_name = BOH
| verifiedrevid = 458977667
| IUPAC_name = 2-(1,3-Benzodioxol-5-yl)-2-methoxyethanamine
| image = BOH Structure.svg


<!--Clinical data-->
<!--Clinical data-->
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| pregnancy_category =
| pregnancy_category =
| legal_status = Uncontrolled
| legal_status = Uncontrolled
| legal_US =[[List of Schedule I drugs|Schedule I (isomer of MDOH)]]
| routes_of_administration = [[Mouth|Oral]]
| routes_of_administration = [[Mouth|Oral]]


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| metabolism =
| metabolism =
| elimination_half-life =
| elimination_half-life =
| excretion =
| excretion =


<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = <!-- blanked - oldvalue: 73304-06-0 -->
| CAS_number = 73304-06-0
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = W7KI9V2RCE
| ATC_prefix = none
| ATC_prefix = none
| ATC_suffix =
| ATC_suffix =
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C10H13NO3/c1-12-10(5-11)7-2-3-8-9(4-7)14-6-13-8/h2-4,10H,5-6,11H2,1H3
| StdInChI = 1S/C10H13NO3/c1-12-10(5-11)7-2-3-8-9(4-7)14-6-13-8/h2-4,10H,5-6,11H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = KUTKTMOZFCYDLZ-UHFFFAOYSA-N
| StdInChIKey = KUTKTMOZFCYDLZ-UHFFFAOYSA-N
| PubChem = 44719487
| PubChem = 44719487
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 21106264
| ChemSpiderID = 21106264


<!--Chemical data-->
<!--Chemical data-->
| C=10 | H=13 | N=1 | O=3
| C=10 | H=13 | N=1 | O=3
| molecular_weight = 195.22 g/mol
| smiles = NCC(OC)c1ccc2OCOc2c1
| smiles = NCC(OC)c1ccc2OCOc2c1
| synonyms = 3,4-methylenedioxy-β-methoxyphenethylamine
| synonyms = 3,4-methylenedioxy-β-methoxyphenethylamine
}}
}}


'''BOH''', also known as '''3,4-methylenedioxy-β-methoxyphenethylamine''', is a [[drug]] of the [[substituted phenethylamine|phenethylamine]] class.<ref name="isbn0-9630096-0-5">{{cite book | author = Ann Shulgin; Alexander Shulgin | title = Pihkal: A Chemical Love Story | publisher = Transform Press | location = | year = 1991 | pages = | isbn = 0-9630096-0-5 | oclc = | doi = | accessdate = }}</ref> It is the β-[[methoxy]] [[analogue (chemistry)|analogue]] of [[methylenedioxyphenethylamine]] (MDPEA), and is also more distantly related to [[methylone]]. On account of its similarity to [[norepinephrine]], the effects of BOH may be of a purely [[adrenergic]] nature.<ref name="isbn0-9630096-0-5">{{cite book | author = Ann Shulgin; Alexander Shulgin | title = Pihkal: A Chemical Love Story | publisher = Transform Press | location = | year = 1991 | pages = | isbn = 0-9630096-0-5 | oclc = | doi = | accessdate = }}</ref>
'''BOH''', also known as '''3,4-methylenedioxy-β-methoxyphenethylamine''', is a [[drug]] of the [[substituted phenethylamine|phenethylamine]] class.<ref name="isbn0-9630096-0-5">{{cite book | vauthors = Shulgin A, Shulgin A | title = Pihkal: A Chemical Love Story | publisher = Transform Press | year = 1991 | isbn = 0-9630096-0-5 | url = http://www.erowid.org/library/books_online/pihkal/pihkal015.shtml}}</ref> It is the β-[[methoxy]] [[structural analog|analog]] of [[methylenedioxyphenethylamine]] (MDPEA) and is also more distantly related to [[methylone]]. On account of its similarity to [[norepinephrine]], the effects of BOH may be of a purely [[adrenergic]] nature.<ref name="isbn0-9630096-0-5"/>


BOH was first [[Chemical synthesis|synthesized]] by [[Alexander Shulgin]].<ref name="isbn0-9630096-0-5">{{cite book | author = Ann Shulgin; Alexander Shulgin | title = Pihkal: A Chemical Love Story | publisher = Transform Press | location = | year = 1991 | pages = | isbn = 0-9630096-0-5 | oclc = | doi = | accessdate = }}</ref> In his book [[PiHKAL]], the dosage range is listed as 80–120&nbsp;mg, and the duration listed as 6–8 hours. Shulgin reports that BOH causes slight [[hyperthermia|warmth]], [[mydriasis]], [[anorexia (symptom)|anorexia]], mild [[nausea]], and [[cold feet]], with no [[psychedelic drug|psychedelic]], [[entactogen]], or [[euphoriant]] effects.<ref name="isbn0-9630096-0-5">{{cite book | author = Ann Shulgin; Alexander Shulgin | title = Pihkal: A Chemical Love Story | publisher = Transform Press | location = | year = 1991 | pages = | isbn = 0-9630096-0-5 | oclc = | doi = | accessdate = }}</ref> He gives it a ++ on the [[Shulgin Rating Scale]].<ref name="isbn0-9630096-0-5">{{cite book | author = Ann Shulgin; Alexander Shulgin | title = Pihkal: A Chemical Love Story | publisher = Transform Press | location = | year = 1991 | pages = | isbn = 0-9630096-0-5 | oclc = | doi = | accessdate = }}</ref> Very little is known about the [[pharmacology]], [[pharmacokinetic]]s, [[therapeutic effect|effect]]s, and [[toxicity]] of BOH.
BOH was first [[Chemical synthesis|synthesized]] by [[Alexander Shulgin]].<ref name="isbn0-9630096-0-5"/> In his book [[PiHKAL]], the dosage range is listed as 80–120&nbsp;mg, and the duration listed as 6–8 hours. Shulgin reports that BOH causes slight [[hyperthermia|warmth]], [[mydriasis]], [[anorexia (symptom)|anorexia]], mild [[nausea]], and [[cold feet]], with no [[psychedelic drug|psychedelic]], [[entactogen]], or [[euphoriant]] effects.<ref name="isbn0-9630096-0-5"/> He gives it a ++ on the [[Shulgin Rating Scale]].<ref name="isbn0-9630096-0-5"/>

==Legality==

===United Kingdom===
This substance is a Class A drug in the [[Drugs controlled by the UK Misuse of Drugs Act#Class A drugs|Drugs controlled by the UK Misuse of Drugs Act]].<ref>{{cite web | title = UK Misuse of Drugs act 2001 Amendment summary | url = http://isomerdesign.com/Cdsa/scheduleUK.php?schedule=1&ion=30&structure=C | access-date = 12 March 2014 | publisher = Isomer Design}}</ref>


== See also ==
== See also ==
* [[BOB (psychedelic)|BOB]]
* [[BOD (psychedelic)|BOD]]
* [[BOHD (psychedelic)|BOHD]]
* [[MDMA]]
* [[Methylenedioxyphenethylamine|MDPEA]]
* [[Methylenedioxyphenethylamine|MDPEA]]
* [[Methylone]]
* [[Methylone]]
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== References ==
== References ==
{{Reflist}}
{{Reflist}}

== External links ==
* [http://www.erowid.org/library/books_online/pihkal/pihkal015.shtml BOH Entry in ''PiHKAL'']
* [http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=15 BOH Entry in PiHKAL • info]



{{Stimulants}}
{{Stimulants}}
{{Monoamine releasing agents}}
{{Adrenergics}}
{{Phenethylamines}}
{{Phenethylamines}}


[[Category:Benzodioxoles]]
[[Category:Benzodioxoles]]
[[Category:Ethers]]
[[Category:Ethers]]
[[Category:Psychedelic phenethylamines]]
[[Category:Phenylethanolamine ethers]]
[[Category:Norepinephrine releasing agents]]