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{{Short description|Psychedelic drug}}
{{one source|date=April 2015}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
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| IUPAC_name = 1-(2,5-dimethoxy-4-propyl-phenyl)propan-2-amine
| Watchedfields = changed
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| image = 2,5-Dimethoxy-4-propylamphetamine.svg
| verifiedrevid = 477211774
| width = 230px
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| IUPAC_name = 1-(2,5-Dimethoxy-4-propylphenyl)propan-2-amine
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| 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
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| image = 2,5-Dimethoxy-4-propylamphetamine.svg
| width = 200px

<!--Clinical data-->
| tradename =
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| pregnancy_category =
| legal_CA = Schedule I
| legal_DE = NpSG
| legal_UK = Class A
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| legal_status =
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| routes_of_administration =

<!--Pharmacokinetic data-->
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| bioavailability =
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| protein_bound =
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| metabolism =
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| elimination_half-life =
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<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
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| CAS_number = 63779-88-4
| CAS_supplemental = <BR> 53581-55-8 (hydrochloride)
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = L3P287BI9W
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| ATC_prefix =
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| ATC_suffix =
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| PubChem = 542051
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
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| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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| ChemSpiderID = 472021
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 8569

<!--Chemical data-->
| C=14 | H=23 | N=1 | O=2
| smiles = O(c1cc(c(OC)cc1CC(N)C)CCC)C
| smiles = O(c1cc(c(OC)cc1CC(N)C)CCC)C
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
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| InChIKey = UEEAUFJYLUJWQJ-UHFFFAOYAM
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| 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
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| CAS_number =
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
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| ATC_prefix =
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| StdInChIKey = UEEAUFJYLUJWQJ-UHFFFAOYSA-N
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| ATC_suffix =
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| synonyms = 2,5-Dimethoxy-4-propylamphetamine
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| PubChem = 542051
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| DrugBank =
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| ChemSpiderID = 472021
| chemical_formula = C<sub14</sub>H<sub>23</sub>NO<sub>2</sub>
| molecular_weight = 237.34 g/mol
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| synonyms = 2,5-dimethoxy-4-propylamphetamine
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| bioavailability =
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| protein_bound =
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| metabolism =
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| elimination_half-life =
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| pregnancy_category=
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| legal_status =
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| routes_of_administration =
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'''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]]{{clear-left}}
[[Image:DOIP_structure.png|180px|thumb|left|Structure of DOIP]]{{clear-left}}


== See also ==
== See also ==
* [[DOPF]]
* [[2,5-Dimethoxy-4-Substituted Amphetamine]]s
* [[DOx]]


== References ==
== 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}}
{{Hallucinogens}}
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{{Phenethylamines}}
{{Phenethylamines}}


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{{DEFAULTSORT:Dimethoxy-4-propylamphetamine, 2,5-}}
[[Category:Substituted amphetamines]]
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[[Category:Designer drugs]]


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{{psychoactive-stub}}


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{{hallucinogen-stub}}
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[[Category:Amphetamines]]
[[Category:2C (psychedelics)]]

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{{DEFAULTSORT:Dimethoxy-4-propylamphetamine, 2,5-}}

Latest revision as of 15:42, 5 October 2024

2,5-Dimethoxy-4-propylamphetamine
Clinical data
Other names2,5-Dimethoxy-4-propylamphetamine
Legal status
Legal status
Identifiers
  • 1-(2,5-Dimethoxy-4-propylphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H23NO2
Molar mass237.343 g·mol−1
3D model (JSmol)
  • O(c1cc(c(OC)cc1CC(N)C)CCC)C
  • 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 ☒N
  • Key:UEEAUFJYLUJWQJ-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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]

Structure of DOIP

See also

[edit]

References

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


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