| Revision as of 18:14, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,071 edits Saving copy of the {{drugbox}} taken from revid 475101821 of page 4-HO-MiPT for the Chem/Drugbox validation project (updated: 'CAS_number'). |
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{{short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{cs1 config|name-list-style=vanc}} |
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{{redirect-distinguish|Miprocin|Mupirocin}} |
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{{Use dmy dates|date=November 2020}} |
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{{more citations needed|date=November 2013}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 464363448 |
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| verifiedrevid = 477222074 |
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| IUPAC_name = 3-(2-ethyl)-1H-indol-4-ol |
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| IUPAC_name = 3-{2-ethyl}-1''H''-indol-4-ol |
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| image = Miprocin.png |
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| width = 140 |
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| image = 4-HO-MiPT.svg |
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| width = 200px |
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| image2 = 4-HO-MiPT-3d-sticks.png |
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| image2 = 4-HO-MiPT-3d-sticks.png |
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| width2 = 160 |
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| width2 = 200px |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = |
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| tradename = |
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| legal_BR = F2 |
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| legal_US = notscheduled |
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| legal_BR_comment = <ref>{{cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=] |language=pt-BR |publication-date=2023-07-25}}</ref> |
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| legal_UK = notscheduled |
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| legal_DE = NpSG |
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| legal_status = See ] |
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| legal_US = Unscheduled |
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| routes_of_administration = Oral, IV, intranasal, rectal |
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| legal_UK = Class A |
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| routes_of_administration = Oral, intranasal, rectal, IV, IM |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| bioavailability = |
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| protein_bound = |
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| protein_bound = |
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| metabolism = Liver |
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| metabolism = |
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| elimination_half-life = 4-6 Hours |
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| elimination_half-life = |
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| excretion = Kidneys/Urine |
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| excretion = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = <!-- blanked - oldvalue: 77872-43-6 --> |
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| CAS_number = 77872-43-6 |
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| ATC_prefix = None |
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| ATC_prefix = None |
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| ATC_suffix = |
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| ATC_suffix = |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 171419 |
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| ChEMBL = 171419 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = 4GAJ9OJ8YZ |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=14 | H=20 | N=2 | O=1 |
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| C=14 | H=20 | N=2 | O=1 |
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| molecular_weight = 232.32 g/mol |
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| smiles = CN(C(C)C)CCC2=CNC1=CC=CC(O)=C12 |
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| smiles = CN(C(C)C)CCC2=CNC1=CC=CC(O)=C12 |
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| InChI = 1/C14H20N2O/c1-10(2)16(3)8-7-11-9-15-12-5-4-6-13(17)14(11)12/h4-6,9-10,15,17H,7-8H2,1-3H3 |
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| InChIKey = RXKGHZCQFXXWFQ-UHFFFAOYAV |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C14H20N2O/c1-10(2)16(3)8-7-11-9-15-12-5-4-6-13(17)14(11)12/h4-6,9-10,15,17H,7-8H2,1-3H3 |
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| StdInChI = 1S/C14H20N2O/c1-10(2)16(3)8-7-11-9-15-12-5-4-6-13(17)14(11)12/h4-6,9-10,15,17H,7-8H2,1-3H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = RXKGHZCQFXXWFQ-UHFFFAOYSA-N |
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| StdInChIKey = RXKGHZCQFXXWFQ-UHFFFAOYSA-N |
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| synonyms = 4-]-''N''-]-''N''-] ] |
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| melting_point = 123 |
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| melting_point = 123 |
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| melting_high = 125 |
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| melting_high = 125 |
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}} |
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}} |
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'''4-HO-MiPT''' ('''miprocin''', '''4-hydroxy-''N''-methyl-''N''-isopropyltryptamine''') is a ] ] ] ] and a lesser-known ] ]. It is thought to be a ], similar to ], ] and ].<ref name=":0">{{cite news |date=2020-01-06 |title=4-HO-MiPT |url=https://psychedelicreview.com/compound/4-ho-mipt/ |access-date=2022-07-05 |website=Psychedelic Science Review |language=en-US}}</ref> Its molecular structure and pharmacological effects somewhat resemble those of the tryptamine ], which is the primary psychoactive chemical in ]. |
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==History== |
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4-HO-MiPT was presumably first ] by ]. Its synthesis is described in his book '']'' along with reports by people who had ingested the compound. Shulgin's trials and other anecdotal information suggest that 4-HO-MiPT is a synthetic psychedelic similar in activity to psilocin. It is relatively uncommon and has only a short history of human use. |
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==Chemistry== |
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Miprocin is the 4-] ] of the chemical ] as well as the isopropyl ] and possible ] of ]. |
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In August 2019, Chadeayne et al. solved the crystal structure of 4-HO-MiPT fumarate.<ref>{{cite journal | vauthors = Chadeayne AR, Pham DN, Golen JA, Manke DR | title = N-methyl derivatives of DMT and psilocin | journal = Acta Crystallographica Section E | volume = 75 | issue = Pt 9 | pages = 1316–1320 | date = September 2019 | pmid = 31523457 | pmc = 6727059 | doi = 10.1107/S2056989019011253 | doi-access = free }}</ref> Its systematic name is (methyl)propan-2-ylazanium 3-carboxyprop-2-enoate monohydrate. The salt consists of a protonated tryptammonium cation and a 3-carboxyacrylate (hydrogen fumarate) anion in the asymmetric unit along with a water molecule of crystallization. |
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==Pharmacology== |
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4-HO-MiPT is thought to be a ] ].<ref name=":0" /> Like other serotonergic psychedelics, its method of action is believed to result from its ] of ] and ] ]s.<ref name=":0" /> |
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==Toxicity== |
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Very little is known about the toxicity of 4-HO-MiPT. Its chemical structure and pharmacological activity are very similar to ], a compound which is not associated with compulsive use or physical dependence. However, because very little research has been done on 4-HO-MiPT, it cannot be definitively concluded that its pharmacological actions in the human body do not differ from those of psilocin. To date, there have been no reported deaths from 4-HO-MiPT.{{citation needed|date=November 2013}} |
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==Duration== |
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Onset of action is 15 to 45 minutes and has a duration of 4 to 6 hours, depending on dose. The duration of action is one half-hour to two hours when injected IV.{{citation needed|date=February 2016}} |
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==Drug prohibition laws== |
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===Sweden=== |
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] health ministry ] classified 4-HO-MiPT as "health hazard" under the act '']'' (translated ''Act on the Prohibition of Certain Goods Dangerous to Health'') as of 1 November 2005, in regulation SFS 2005:733 listed as "4-hydroxi-N,N-metylisopropyltryptamin (4-HO-MIPT)", making it illegal to sell or possess.<ref>{{cite web | title = Förordning om ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor | language = Swedish | trans-title = Regulation amending the Ordinance (1999: 58) on Prohibition against certain dangerous goods | url = http://www.notisum.se/rnp/sls/sfs/20050733.pdf | work = Swedish Code of Statutes | date = 6 October 2005 | access-date = 6 September 2013 | archive-date = 26 June 2021 | archive-url = https://web.archive.org/web/20210626164247/http://www.notisum.se/rnp/sls/sfs/20050733.pdf | url-status = dead }}</ref> |
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===United Kingdom=== |
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The substance could also be considered illegal in the UK under the ]. |
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===United States=== |
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4-HO-MiPT is an unscheduled drug in the United States. However, it is arguably an ] of psilocin, which could lead to prosecution under the ]. |
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===Russia=== |
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4-HO-MiPT is in Schedule 1 in Russia as an analog of 4-hydroxytryptamine. |
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== See also == |
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== References == |
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{{Reflist}} |
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== External links == |
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{{Hallucinogens}} |
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{{Serotonergics}} |
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{{Tryptamines}} |
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{{DEFAULTSORT:4-Ho-Mipt}} |
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