2,5-Dimethoxy-4-propylamphetamine: Difference between revisions

2,5-Dimethoxy-4-propylamphetamine
Clinical data
Other names	2,5-Dimethoxy-4-propylamphetamine
Legal status
Legal status	CA: Schedule I; DE: NpSG (Industrial and scientific use only); UK: Class A;
Identifiers
	IUPAC name 1-(2,5-Dimethoxy-4-propylphenyl)propan-2-amine;
CAS Number	63779-88-4 ; 53581-55-8 (hydrochloride);
PubChem CID	542051;
ChemSpider	472021 ;
UNII	L3P287BI9W;
ChEMBL	ChEMBL8569 ;
CompTox Dashboard (EPA)	DTXSID40337347 ;
Chemical and physical data
Formula	C14H23NO2
Molar mass	237.343 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O(c1cc(c(OC)cc1CC(N)C)CCC)C;
	InChI InChI=1S/C15H25NO2/c1-5-6-11-8-14(17-4)12(7-10(2)15)9-13(11)16-3/h8-10H,5-7,15H2,1-4H3 ; Key:UEEAUFJYLUJWQJ-UHFFFAOYSA-N ;
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Latest revision as of 15:42, 5 October 2024

2,5-Dimethoxy-4-propylamphetamine (DOPR) is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized by Alexander Shulgin, and was described in his book PiHKAL (Phenethylamines i Have Known And Loved). Shulgin described DOPR as a "heavy duty psychedelic", complete with alterations of the thought process and visual distortion.^[1] Very little data exists about the pharmacological properties, metabolism, and toxicity of DOPR.

The alternative structural isomer DOIP, with a 4-isopropyl substitution, is also known but is around ten times weaker than DOPR, with an active dose of some 20–30 mg (as compared to 2–5 mg for DOPR).^[1]

References

^ ^a ^b Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. United States: Transform Press. p. 978. ISBN 0-9630096-0-5.

This hallucinogen-related article is a stub. You can help Wikipedia by expanding it.

[PiHKAL-1] Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. United States: Transform Press. p. 978. ISBN 0-9630096-0-5.

[1]

@@ Line 1: / Line 1: @@
+{{Short description|Psychedelic drug}}
+{{one source|date=April 2015}}
 {{Drugbox
+| Verifiedfields = changed
-| verifiedrevid = 413105637
+| Watchedfields = changed
-| IUPAC_name        = 1-(2,5-dimethoxy-4-propyl-phenyl)propan-2-amine
+| verifiedrevid = 477211774
-| image             = 2,5-Dimethoxy-4-propylamphetamine.svg
+| IUPAC_name = 1-(2,5-Dimethoxy-4-propylphenyl)propan-2-amine
-| width             = 230px
+| image = 2,5-Dimethoxy-4-propylamphetamine.svg
-| InChI = 1/C14H23NO2/c1-5-6-11-8-14(17-4)12(7-10(2)15)9-13(11)16-3/h8-10H,5-7,15H2,1-4H3
+| width = 200px
-| smiles = O(c1cc(c(OC)cc1CC(N)C)CCC)C
-| InChIKey = UEEAUFJYLUJWQJ-UHFFFAOYAM
+<!--Clinical data-->
+| tradename =
+| pregnancy_category =
+| legal_CA = Schedule I
+| legal_DE = NpSG
+| legal_UK = Class A
+| legal_status =
+| routes_of_administration =
+<!--Pharmacokinetic data-->
+| bioavailability =
+| protein_bound =
+| metabolism =
+| elimination_half-life =
+| excretion =
+<!--Identifiers-->
+| CAS_number_Ref = {{cascite|changed|??}}
+| CAS_number = 63779-88-4
+| CAS_supplemental = <BR> 53581-55-8 (hydrochloride)
+| UNII_Ref = {{fdacite|correct|FDA}}
+| UNII = L3P287BI9W
+| ATC_prefix =
+| ATC_suffix =
+| PubChem = 542051
+| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
+| DrugBank =
+| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
+| ChemSpiderID = 472021
 | ChEMBL_Ref = {{ebicite|correct|EBI}}
 | ChEMBL = 8569
-| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
+<!--Chemical data-->
-| StdInChI = 1S/C14H23NO2/c1-5-6-11-8-14(17-4)12(7-10(2)15)9-13(11)16-3/h8-10H,5-7,15H2,1-4H3
+| C=14 | H=23 | N=1 | O=2
+| smiles = O(c1cc(c(OC)cc1CC(N)C)CCC)C
+| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
+| StdInChI = 1S/C15H25NO2/c1-5-6-11-8-14(17-4)12(7-10(2)15)9-13(11)16-3/h8-10H,5-7,15H2,1-4H3
 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
 | StdInChIKey = UEEAUFJYLUJWQJ-UHFFFAOYSA-N
+| synonyms = 2,5-Dimethoxy-4-propylamphetamine
-| CAS_number        =
-| ATC_prefix        =
-| ATC_suffix        =
-| PubChem           = 542051
-| DrugBank          =
-| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
-| ChemSpiderID      = 472021
-| chemical_formula  = C<sub>14</sub>H<sub>23</sub>NO<sub>2</sub>
-| molecular_weight  = 237.34 g/mol
-| synonyms          = 2,5-dimethoxy-4-propylamphetamine
-| bioavailability   =
-| protein_bound     =
-| metabolism        =
-| elimination_half-life =
-| excretion         =
-| pregnancy_category=
-| legal_status      =
-| routes_of_administration =
 }}
-'''2,5-Dimethoxy-4-propylamphetamine''' ('''DOPR''') is a [[psychedelic_drug|psychedelic]] [[drug]] of the [[substituted phenethylamine|phenethylamine]] and [[substituted amphetamine|amphetamine]] [[chemical class]]es. It was first [[synthesis|synthesized]] by [[Alexander Shulgin]], and was described in his book ''[[PiHKAL]]'' (''Phenethylamines i Have Known And Loved''). Shulgin described DOPR is a "heavy duty psychedelic", complete with alterations of the thought process and visual distortion, and gave his experience with it a +++ on the [[Shulgin Rating Scale]].<ref name="PiHKAL">{{cite book | title = PiHKAL: A Chemical Love Story | last = Shulgin | first = Alexander | coauthors = Shulgin, Ann | month = September | year = 1991 | publisher = Transform Press | location = United States | isbn = 0-9630096-0-5 | pages = 978 | url = http://www.erowid.org/library/books_online/pihkal/pihkal.shtml}}</ref> Very little data exists about the pharmacological properties, metabolism, and toxicity of DOPR.
+'''2,5-Dimethoxy-4-propylamphetamine''' ('''DOPR''') is a [[psychedelic drug|psychedelic]] [[drug]] of the [[substituted phenethylamine|phenethylamine]] and [[substituted amphetamine|amphetamine]] [[chemical class]]es. It was first [[Organic synthesis|synthesized]] by [[Alexander Shulgin]], and was described in his book ''[[PiHKAL]]'' (''Phenethylamines i Have Known And Loved''). Shulgin described DOPR as a "heavy duty psychedelic", complete with alterations of the thought process and visual distortion.<ref name="PiHKAL">{{cite book | title = PiHKAL: A Chemical Love Story | vauthors = Shulgin A, Shulgin A | publisher = Transform Press | location = United States | isbn = 0-9630096-0-5 | pages = 978 | url = http://www.erowid.org/library/books_online/pihkal/pihkal.shtml |date= September 1991}}</ref> Very little data exists about the pharmacological properties, metabolism, and toxicity of DOPR.
-The alternative structural isomer DOIP, with a 4-isopropyl substitution, is also known but is around ten times weaker than DOPR, with an active dose of some 20-30mg (as compared to 2-5mg for DOPR).<ref name="PiHKAL">{{cite book | title = PiHKAL: A Chemical Love Story | last = Shulgin | first = Alexander | coauthors = Shulgin, Ann | month = September | year = 1991 | publisher = Transform Press | location = United States | isbn = 0-9630096-0-5 | pages = 978 | url = http://www.erowid.org/library/books_online/pihkal/pihkal.shtml}}</ref>
+The alternative structural isomer [[2,5-Dimethoxy-4-isopropylamphetamine|DOIP]], with a 4-isopropyl substitution, is also known but is around ten times weaker than DOPR, with an active dose of some 20–30&nbsp;mg (as compared to 2–5&nbsp;mg for DOPR).<ref name="PiHKAL"/>
 [[Image:DOIP_structure.png|180px|thumb|left|Structure of DOIP]]{{clear-left}}
 == See also ==
+* [[DOPF]]
-* [[2,5-Dimethoxy-4-Substituted Amphetamine]]s
+* [[DOx]]
 == References ==
-{{Reflist|2}}
+{{Reflist}}
-== External links ==
-* [http://www.erowid.org/library/books_online/pihkal/pihkal071.shtml DOPR Entry in ''PiHKAL'']
-* [http://pihkal.info/read.php?domain=pk&id=71 DOPR Entry in PiHKAL • info]
 {{Hallucinogens}}
 {{Serotonergics}}
 {{Phenethylamines}}
-[[Category:Amphetamines]]
-[[Category:2C (psychedelics)]]
 {{DEFAULTSORT:Dimethoxy-4-propylamphetamine, 2,5-}}
+[[Category:Substituted amphetamines]]
+[[Category:Designer drugs]]
-{{nervous-system-drug-stub}}
+{{hallucinogen-stub}}

v t e Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-AL 3C-BZ 3C-E 3C-MAL 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA ZDCM-04 Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D-Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D-DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L-DOPA (Levodopa) L-DOPS (Droxidopa) L-Phenylalanine L-Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101 Venlafaxine