Psychedelic Research Chemicals or RC Chems are new synthetic substances which are structurally similar to the original drug, while being functional analogs. Data on their effects limited due as they’re fairly new and do not have a lot of human consumption history.

Psychedelics are substances (natural or laboratory made) which cause profound changes in a one’s perceptions of reality. While under the influence of hallucinogens, users might hallcuniate visually and auditorily.

Disclaimer: Psychedelic drugs offer some of the most powerful and intense psychological experiences. Additionally these substances are illegal in many places. We understand that even though these substances are illegal, their use occurs frequently. We do not condone breaking of the law. By providing accurate information about these substances, we encourage the user to make responsible decisions and practice harm reduction.

Read the full disclaimer here.

Description

DOI Also known as:

  • 1-(4-Iod-2,5-dimethoxyphenyl)-2-propanamin[German][ACD/IUPAC Name]
  • 1-(4-Iodo-2,5-dimethoxyphenyl)-2-propanamine[ACD/IUPAC Name]
  • 1-(4-Iodo-2,5-diméthoxyphényl)-2-propanamine[French][ACD/IUPAC Name]
  • 1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine
  • 2,5-Dimethoxy-4-iodoamphetamine
  • 2,5-dimethoxy-4-iodophenylisopropylamine
  • 4-DOI[Formula]
  • 4-iodo-2,5-dimethoxyphenylisopropylamine
  • 4-iodo-2,5-dimethoxyphenylisopropylamine, (±)-isomer
  • 4-iodo-2,5-dimethoxy-α-methylbenzeneethanamine
  • Benzeneethanamine, 4-iodo-2,5-dimethoxy-α-methyl-[ACD/Index Name]
  • (±)2-(4-Iodo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine
  • (±)-2,5-DIMETHOXY-4-IODOAMPHETAMINE
  • [64584-34-5]
  • 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane
  • 1-(2,5-Dimethoxy-4-Iodophenyl)-Propan-2-amine
  • 1-(4-iodo-2,5-dimethoxyphenyl)-2-aminopropane
  • 1-(4-jodo-2,5-dimethoxyphenyl)propan-2-amine[ACD/IUPAC Name]
  • 2-(4-iodo-2,5-dimethoxyphenyl)-1-methylethylamine
  • 2-(4-Iodo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine
  • 2-(4-Iodo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine(DOI)
  • 2-(4-Iodo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine[(±) DOI]
  • 4-Iodo-2,5-dimethoxyamphetamine
  • 4-iodo-3-methoxy-N-(1-methoxypropan-2-yl)aniline
  • amphetamine, 2,5-dimethoxy-4-iodo-
  • DOI
  • DOI-P
  • MFCD05662244[MDL number]

A potent, long-acting psychedelic stimulant. Historically, it has rarely been consumed deliberately, but occasionally sold as LSD. However, it has recently found its own little nest in the research chemical community.

Summary

It is a member of the DOx family of psychedelic amphetamines. The synthesis of DOI was first reported in 1972 and its usage in humans was first documented by Alexander Shulgin in the 1991 book PiHKAL ("Phenethylamines I Have Known and Loved"). DOI is very well-researched compared to most psychedelics.

It is regularly used in research as a radioligand to map serotonin-2A receptors in the brain. The effects of DOI are often compared to those of LSD, although notable differences can be distinguished. Besides the significantly longer duration, the experience is commonly reported to be more stimulating than LSD, with a more pronounced body load and a less complex head space.

The after effects include long-lasting residual stimulation and difficulty sleeping, which, depending on the dose and time taken during the day, may persist for days afterwards. DOI is sometimes sold as a substitute for LSD, or even sold falsely as LSD. This can be dangerous because DOI does not have the same established safety profile as LSD.

Along with its sensitive dose-response and unusually long duration, many reports also suggest that this substance may be overly difficult to use safely for those who are not already experienced with psychedelics. Therefore it is highly advised to approach this highly dose-sensitive, and long-lasting psychedelic substance with the proper amount of precaution and harm reduction practices if using it.

History

DOI was first synthesized by a team at the University of Alberta in 1972. ResearchNeuroplasticityOne study demonstrated that DOI, DMT, LSD, and noribogaine (a metabolite of ibogain) promotes neuritogenesis both in vitro and in vivo.

Chemistry

Amphetamines are substituted phenethylamines containing a phenyl ring bound to an amino (NH2) group through an ethyl chain and a methyl group bound to the alpha carbon Rα.

DOI contains methoxy functional groups OCH3 attached to carbons R2 and R5 as well as an iodine atom attached to carbon R4 of the phenyl ring.

DOI is the amphetamine, or alpha-methylated analogue, of the phenethylamine 2C-I.

Common Name2,5-dimethoxy-4-iodophenylisopropylamine
Systematic name2,5-dimethoxy-4-iodophenylisopropylamine
FormulaC_{11}H_{16}INO_{2}
SMILESCC(Cc1cc(c(cc1OC)I)OC)N
Std. InChiInChI=1S/C11H16INO2/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2/h5-7H,4,13H2,1-3H3
Std. InChiKeyBGMZUEKZENQUJY-UHFFFAOYSA-N
Avg. Mass321.1547 Da
Molecular Weight321.1547
Monoisotopic Mass321.022552 Da
Nominal Mass321
ChemSpider ID1192

Become an Exclusive Member For Free

Become a member now, sign up, and get free updates, news articles, and the latest happenings in the Psychedelic World.

Dose Chart

Oral
Threshold500-750ug.
Light750ug-1mg.
Common1mg-3mg.
Heavy3mg+

Duration Chart

DOI Duration Data
Onset60-90 minutes
Duration12-18 hours
After-effects1-24 hours

Interactions

Caution

  1. Mescaline
  2. NBOMes
  3. 2C-x
  4. 2C-T-x
  5. 5-MeO-xxT
    • The 5-MeO class of tryptamines can be unpredictable in their interactions, particularly increasing the risk of unpleasant physical side effects.
  6. Cannabis
    • Cannabis has an unexpectedly strong and somewhat unpredictable synergy with psychedelics.
  7. MXE
    • As an NMDA antagonist MXE potentiates DOx which can be unpleasantly intense
  8. MDMA
    • The combined stimulating effects of the two can be uncomfortable. Coming down on the MDMA while the DOx is still active can be quite anxiogenic.
  9. Caffeine
    • High doses of caffeine may cause anxiety which is less manageable when tripping, and since both are stimulating it may cause some physical discomfort.
  10. MAOIs
    • MAO-B inhibitors can increase the potency and duration of phenethylamines unpredictably

Dangerous

  1. DXM
    • The DOx class as psychedelic stimulants have the potential to mask the effects of DXM and could lead to redosing to an unsafe level. DXM can also potentiate DOx resulting in an unpleasantly intense experience.
  2. PCP
    • Details of this combination are not well understood but PCP generally interacts in an unpredictable manner.
  3. Amphetamines
    • The combined stimulating effects of the two can lead to an uncomfortable body-load, while the focusing effects of amphetamine can easily lead to thought loops. Coming down from amphetamines while the DOx is still active can be quite anxiogenic.
  4. Cocaine
    • The combined stimulating effects of the two can lead to an uncomfortable body-load, while the focusing effects of cocaine can easily lead to thought loops. Coming down from cocaine while the DOx is still active can be quite anxiogenic
  5. Tramadol
    • Tramadol is well known to lower seizure threshold and psychedelics also cause occasional seizures.

Low Synergy

  1. Alcohol
    • Drinking on stimulants is risky because the sedative effects of the alcohol are reduced, and these are what the body uses to gauge drunkenness. This typically leads to excessive drinking with greatly reduced inhibitions, high risk of liver damage and increased dehydration. They will also allow you to drink past a point where you might normally pass out, increasing the risk.
  2. GHB/GBL
  3. Benzodiazepines
  4. SSRIs

No Synergy

  1. Opioids
    • No unexpected interactions.

High Synergy

  1. Mushrooms
  2. LSD
  3. DMT
  4. Ketamine
    • Ketamine and psychedelics tend to potentiate each other - go slowly.
  5. N2O

Legal Status

  • Australia: DOI is not listed as a prohibited substance in The Standard for the Uniform Scheduling of Medicines and Poisons (SUSMP).
  • Austria: DOI is illegal to possess, produce and sell under the NPSG (Neue-Psychoaktive-Substanzen-Gesetz Österreich).
  • Brazil: DOI is illegal to possess, produce and sell as it is listed on Portaria SVS/MS nº 344.
  • Canada: DOI is listed as a Schedule 1 drug as it is an analogue of amphetamine. The CDSA was updated as a result of the Safe Streets Act changing amphetamines from Schedule 3 to Schedule 1.
  • Denmark: DOI became illegal on April 8, 2007.
  • Germany: DOI is controlled under Anlage II BtMG (Narcotics Act, Schedule II) as of December 13, 2014. It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.
  • Latvia: DOI is a Schedule I controlled substance.
  • Sweden: DOI is a Schedule I substance as of August 30, 2007; this was published by the Medical Products Agency in their regulation LVFS 2007:10.
  • United Kingdom: DOI is illegal to produce, supply, or import under the Psychoactive Substance Act, which came into effect on May 26th, 2016.
  • United States: DOI is not scheduled in the United States, but it is likely that it would be considered an analog (of DOB) in which case sales or possession could be prosecuted under the Federal Analogue Act. DOI is regularly used in animal and in vitro research.
    • Florida: DOI is a Schedule I controlled substance in the state of Florida.

    • Sources

    References

    1. Coutts, R. T., & Malicky, J. L. (1973). The synthesis of some analogs of the hallucinogen 1-(2, 5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM). Canadian Journal of Chemistry, 51(9), 1402-1409. https://doi.org/10.1139/v73-210
    2. Cite error: Invalid <ref> tag; no text was provided for refs named DOI TiHKAL
    3. LSD BLOTTER ACID MIMICS (ACTUALLY CONTAINING 4-IODO-2,5-DIMETHOXYAMPHETAMINE (DOI) AND 4-CHLORO-2,5-DIMETHOXYAMPHETAMINE (DOC)) IN LANTANA, FLORIDA | http://web.archive.org/web/20090204025435/http://www.usdoj.gov/dea/programs/forensicsci/microgram/mg0608/mg0608.html
    4. Coutts, R. T., & Malicky, J. L. (1973). The synthesis of some analogs of the hallucinogen 1-(2, 5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM). Canadian Journal of Chemistry, 51(9), 1402-1409. https://doi.org/10.1139/v73-210
    5. https://www.cell.com/cell-reports/fulltext/S2211-1247(18)30755-1
    6. http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=67
    7. Head-twitch response in rodents induced by the hallucinogen 2,5-dimethoxy-4-iodoamphetamine: a comprehensive history, a re-evaluation of mechanisms, and its utility as a model (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/22517680
    8. Serotonin 5-Hydroxytryptamine2A Receptor Activation Suppresses Tumor Necrosis Factor-α-Induced Inflammation with Extraordinary Potency | Journal of Pharmacology and Experimental Therapeutics (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/18708586
    9. Jones, K. A., Srivastava, D. P., Allen, J. A., Strachan, R. T., Roth, B. L., & Penzes, P. (2009). Rapid modulation of spine morphology by the 5-HT2A serotonin receptor through kalirin-7 signaling. Proceedings of the National Academy of Sciences, 106(46), 19575-19580. PMID: 19889983. https://doi.org/10.1073/pnas.0905884106
    10. Talaie, H., Panahandeh, R., Fayaznouri, M. R., Asadi, Z., & Abdollahi, M. (2009). Dose-independent occurrence of seizure with tramadol. Journal of medical toxicology, 5(2), 63-67. doi:10.1007/BF03161089
    11. Therapeutic Goods Administration. Australian Government Department of Health and Ageing | http://www.comlaw.gov.au/Details/F2013L01607/229bdf2e-7014-4379-b751-0b584f55d699
    12. http://portal.anvisa.gov.br/documents/10181/3115436/(1)RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7
    13. Canadian Legal Information Institute (CanLII). Controlled Drugs and Substances Act, S.C. 1996, c. 19, as amended | http://isomerdesign.com/Cdsa/schedule.php?schedule=1&section=18.5&structure=C
    14. Canadian Legal Information Institute (CanLII). Controlled Drugs and Substances Act, S.C. 1996, c. 19, as amended | http://isomerdesign.com/Cdsa/definitions.php?structure=C
    15. "Achtundzwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften" (in German). Bundesanzeiger Verlag. Retrieved December 11, 2019.
    16. "Anlage II BtMG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 11, 2019.
    17. "§ 29 BtMG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 11, 2019.
    18. Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem (2,5-Dimetoksifeniletānamīni) | http://likumi.lv/doc.php?id=121086
    19. Läkemedelsverkets författningssamling | http://www.lakemedelsverket.se/upload/lvfs/LVFS_2007-10.pdf
    20. Psychoactive Substances Act 2016 (Legislation.gov.uk) | http://www.legislation.gov.uk/ukpga/2016/2/contents/enacted
    21. The 2015 Florida Statutes Title XLVI CRIMES Chapter 893 DRUG ABUSE PREVENTION AND CONTROL | http://leg.state.fl.us/statutes/index.cfm?App_mode=Display_Statute&URL=0800-0899/0893/0893.html

    Resources

    1. 1717 CheMall OR019354
    2. 1717 CheMall OR142131
    3. abcr AB464221
    4. ABI Chemicals AC1Q1QZQ
    5. AK Scientific 9890AB
    6. AKos AKOS015965128
    7. Alichem A019126275
    8. Amadis Chemical A834816
    9. American Custom Chemicals Corp API0007571
    10. Ark Pharm, Inc. AK121885
    11. Atomax jiji41520
    12. Aurora Fine Chemicals A13.112.957
    13. Aurora Fine Chemicals K02.874.540
    14. BePharm B51181
    15. BGS International BG01295390
    16. BGS International BG04659983
    17. BindingDB 28582
    18. BOC Sciences 64584-34-5
    19. CEG Chemical QC-2023
    20. ChEBI
    21. ChEBI CHEBI:64629
    22. ChEMBL CHEMBL6616
    23. Chembo Pharma KB-214892
    24. ChemDB 3963965
    25. ChemIDplus 064584345
    26. ChemIDplus 64584345
    27. Chemspace CSC020626781
    28. Collaborative Drug Discovery 215462
    29. Collaborative Drug Discovery 41412
    30. Comparative Toxicogenomics Database C015952
    31. DiscoveryGate 1229
    32. eMolecules 536778
    33. eNovation Chemicals K49059
    34. EPA DSSTox DTXCID5020520
    35. FDA UNII - NLM OOM10GW9UE
    36. Finetech Industry FT-0666888
    37. Guide to PHARMACOLOGY 147
    38. iChemical EBD70731
    39. LabNetwork
    40. LabNetwork LN00201101
    41. LeadScope LS-176383
    42. Matrix Scientific 100662
    43. Mcule MCULE-2915700352
    44. NIST Spectra mainlib_334995
    45. NMRShiftDB 20182597
    46. OXchem
    47. OXchem AX8051181
    48. PIChemicals PI-36596
    49. PubChem 1229
    50. PubMed 10027508
    51. PubMed 10334495
    52. PubMed 10378235
    53. PubMed 10391482
    54. PubMed 10422888
    55. PubMed 10435391
    56. PubMed 10454145
    57. PubMed 10465692
    58. PubMed 10516629
    59. PubMed 10549818
    60. PubMed 10594338
    61. PubMed 10615251
    62. PubMed 10646521
    63. PubMed 10647096
    64. PubMed 10734159
    65. PubMed 10832606
    66. PubMed 10974606
    67. PubMed 10996140
    68. PubMed 11125740
    69. PubMed 11145190
    70. PubMed 11198134
    71. PubMed 11259568
    72. PubMed 11382861
    73. PubMed 11426831
    74. PubMed 11509227
    75. PubMed 11513358
    76. PubMed 11517239
    77. PubMed 11518476
    78. PubMed 11570703
    79. PubMed 11641454
    80. PubMed 11711213
    81. PubMed 11714872
    82. PubMed 11733692
    83. PubMed 11739593
    84. PubMed 11807839
    85. PubMed 11813245
    86. PubMed 11861331
    87. PubMed 11900808
    88. PubMed 11906967
    89. PubMed 12020863
    90. PubMed 12031852
    91. PubMed 12079687
    92. PubMed 12191650
    93. PubMed 12213545
    94. PubMed 12384165
    95. PubMed 12417689
    96. PubMed 12424552
    97. PubMed 12474110
    98. PubMed 12486201
    99. PubMed 12496939
    100. PubMed 12498911
    101. PubMed 12695874
    102. PubMed 12726823
    103. PubMed 12853103
    104. PubMed 12866717
    105. PubMed 12892833
    106. PubMed 12905103
    107. PubMed 12909198
    108. PubMed 1326439
    109. PubMed 1328893
    110. PubMed 1333084
    111. PubMed 1333974
    112. PubMed 1334504
    113. PubMed 1336759
    114. PubMed 1355968
    115. PubMed 1357158
    116. PubMed 1358651
    117. PubMed 1362158
    118. PubMed 1363616
    119. PubMed 1365860
    120. PubMed 1385172
    121. PubMed 1387198
    122. PubMed 1388247
    123. PubMed 1407403
    124. PubMed 1409796
    125. PubMed 1409811
    126. PubMed 1422575
    127. PubMed 1448177
    128. PubMed 14499146
    129. PubMed 1451731
    130. PubMed 14586538
    131. PubMed 14638487
    132. PubMed 14646242
    133. PubMed 14665977
    134. PubMed 1467825
    135. PubMed 1473565
    136. PubMed 14744596
    137. PubMed 1499656
    138. PubMed 15016478
    139. PubMed 15064330
    140. PubMed 1508309
    141. PubMed 1521159
    142. PubMed 15270248
    143. PubMed 1535317
    144. PubMed 15596395
    145. PubMed 1560361
    146. PubMed 15733547
    147. PubMed 15767844
    148. PubMed 15777774
    149. PubMed 1596688
    150. PubMed 1601066
    151. PubMed 16054778
    152. PubMed 16098683
    153. PubMed 16289351
    154. PubMed 16313900
    155. PubMed 16314884
    156. PubMed 16326032
    157. PubMed 16377963
    158. PubMed 16510485
    159. PubMed 1665919
    160. PubMed 1667289
    161. PubMed 16759803
    162. PubMed 16788811
    163. PubMed 1686200
    164. PubMed 1691671
    165. PubMed 17051415
    166. PubMed 17056873
    167. PubMed 17059817
    168. PubMed 17159160
    169. PubMed 17203014
    170. PubMed 17222492
    171. PubMed 17293055
    172. PubMed 17333133
    173. PubMed 17350760
    174. PubMed 17493641
    175. PubMed 17584957
    176. PubMed 1762059
    177. PubMed 17623018
    178. PubMed 17632045
    179. PubMed 17646429
    180. PubMed 17721644
    181. PubMed 17727968
    182. PubMed 1797303
    183. PubMed 1837523
    184. PubMed 1837848
    185. PubMed 1839066
    186. PubMed 1839384
    187. PubMed 1951703
    188. PubMed 1967969
    189. PubMed 1968846
    190. PubMed 2109269
    191. PubMed 2127400
    192. PubMed 2138338
    193. PubMed 2144825
    194. PubMed 2149668
    195. PubMed 2150180
    196. PubMed 2150776
    197. PubMed 2182326
    198. PubMed 2225358
    199. PubMed 2243353
    200. PubMed 2250559
    201. PubMed 2263671
    202. PubMed 2282932
    203. PubMed 2357566
    204. PubMed 2455040
    205. PubMed 2524390
    206. PubMed 2790491
    207. PubMed 2943960
    208. PubMed 2958619
    209. PubMed 2965025
    210. PubMed 2970973
    211. PubMed 3128809
    212. PubMed 3252260
    213. PubMed 3402537
    214. PubMed 3416918
    215. PubMed 3613863
    216. PubMed 592317
    217. PubMed 7504133
    218. PubMed 7506633
    219. PubMed 7531851
    220. PubMed 7682702
    221. PubMed 7862829
    222. PubMed 7870905
    223. PubMed 7904049
    224. PubMed 7904565
    225. PubMed 7907025
    226. PubMed 7907518
    227. PubMed 8093723
    228. PubMed 8095238
    229. PubMed 8095465
    230. PubMed 8097247
    231. PubMed 8101639
    232. PubMed 8104640
    233. PubMed 8145893
    234. PubMed 8149973
    235. PubMed 8158279
    236. PubMed 8208779
    237. PubMed 8265689
    238. PubMed 8268033
    239. PubMed 8273284
    240. PubMed 8276064
    241. PubMed 8282013
    242. PubMed 8282022
    243. PubMed 8301554
    244. PubMed 8344205
    245. PubMed 8350262
    246. PubMed 8355216
    247. PubMed 8382263
    248. PubMed 8386213
    249. PubMed 8386861
    250. PubMed 8394920
    251. PubMed 8420788
    252. PubMed 8435750
    253. PubMed 8436806
    254. PubMed 8446921
    255. PubMed 8448594
    256. PubMed 8472747
    257. PubMed 8474019
    258. PubMed 8492912
    259. PubMed 9106912
    260. PubMed 9130298
    261. PubMed 9152385
    262. PubMed 9262333
    263. PubMed 9373681
    264. PubMed 9401707
    265. PubMed 9404824
    266. PubMed 9422298
    267. PubMed 9423936
    268. PubMed 9427365
    269. PubMed 9435197
    270. PubMed 9507167
    271. PubMed 9539263
    272. PubMed 9570460
    273. PubMed 9597673
    274. PubMed 9644038
    275. PubMed 9676898
    276. PubMed 9681934
    277. PubMed 9683007
    278. PubMed 9748522
    279. PubMed 9751178
    280. PubMed 9754805
    281. PubMed 9768567
    282. PubMed 9843894
    283. PubMed 9863644
    284. PubMed 9867239
    285. PubMed 9888626
    286. PubMed 9926825
    287. Royal Society of Chemistry B906391A
    288. SORD SST0025416
    289. Springer Nature From Rodents to Recovery
    290. Thomson Pharma 00041989
    291. Tractus Company Limited
    292. Wikidata Q209251
    293. Wikipedia 2,5-Dimethoxy-4-iodoamphetamine
    294. xPharm 8347

    Information made possible with:

    1. PsychonautWiki is a community-driven online encyclopedia that aims to document the field of psychonautics in a comprehensive, scientifically-grounded manner.
    2. Erowid is a non-profit educational & harm-reduction resource with 60 thousand pages of online information about psychoactive drugs
    3. PubChem National Center for Bio Informatics
    4. Chemspider is a free chemical structure database providing fast access to over 34 million structures, properties and associated information.
    5. Wikipedia

    Additional APIs were used to construct this information. Thanks to ChemSpider, NCBI, PubChem etc.

    Data is constantly updated so please check back later to see if there is any more available information on this substance.