From Wikipedia, the free encyclopedia
Pharmaceutical compound
βk-2C-I |
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| Other names | bk-2C-I; β-Keto-2C-I; β-Keto-4-iodo-2,5-dimethoxyphenethylamine; 4-Iodo-2,5-dimethoxy-β-ketophenylethylamine; 4′-Iodo-2′,5′-dimethoxy-2-aminoacetophenone; 4-Iodo-2,5-dimethoxycathinone; 2,5MeO,4I-AcP |
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| Drug class | Serotonergic psychedelic; Hallucinogen |
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| ATC code | |
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2-amino-1-(4-iodo-2,5-dimethoxyphenyl)ethanone
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| PubChem CID | |
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| CompTox Dashboard (EPA) | |
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| Formula | C10H12INO3 |
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| Molar mass | 321.114 g·mol−1 |
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| 3D model (JSmol) | |
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COC1=CC(=C(C=C1C(=O)CN)OC)I
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InChI=1S/C10H12INO3/c1-14-9-4-7(11)10(15-2)3-6(9)8(13)5-12/h3-4H,5,12H2,1-2H3 Key:SGQREGRMRKZYSF-UHFFFAOYSA-N
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βk-2C-I, or bk-2C-I, also known as β-keto-4-iodo-2,5-dimethoxyphenethylamine or as β-keto-2C-I, is a psychedelic drug of the phenethylamine and 2C families related to 2C-I.[1][2] It is the β-keto derivative of 2C-I and is cathinone-like in chemical structure.[1][2] The drug is closely related to βk-2C-B.[1][2] It is said to have a longer duration than 2C-I and to not be as intense in its effects as βk-2C-B.[1] Concerns have been expressed about the potential toxicity of the iodine in βk-2C-I.[1] The interactions of βk-2C-I with monoamine oxidase have been studied.[2] βk-2C-I was encountered as a novel designer drug online by at least 2016 and was first described in the scientific literature by 2018.[1] βk-2C-I is a controlled substance in Canada under phenethylamine blanket-ban language.[3]
- ^ a b c d e f Texter KB, Waymach R, Kavanagh PV, O'Brien JE, Talbot B, Brandt SD, et al. (January 2018). "Identification of pyrolysis products of the new psychoactive substance 2-amino-1-(4-bromo-2,5-dimethoxyphenyl)ethanone hydrochloride (bk-2C-B) and its iodo analogue bk-2C-I" (PDF). Drug Testing and Analysis. 10 (1): 229–236. doi:10.1002/dta.2200. PMID 28371351.
The general consensus is that bk-2C-B lasts about 10 h, noticeably longer than 2C–B. Negative effects of snorting include severe burning and purple mucus. Gastrointestinal effects including severe diarrhoea are also common.[13] The few user reports on the forums indicate that bk-2C-I also lasts longer, but does not produce as intense a high as bk-2C-I. Concerns were expressed about the toxicity of iodine.
- ^ a b c d Wagmann L, Brandt SD, Stratford A, Maurer HH, Meyer MR (February 2019). "Interactions of phenethylamine-derived psychoactive substances of the 2C-series with human monoamine oxidases" (PDF). Drug Testing and Analysis. 11 (2): 318–324. doi:10.1002/dta.2494. PMID 30188017.
- ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
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| | No ring subs. | |
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| 4-Hydroxytryptamines | |
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| 5-Hydroxytryptamines | |
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| 5-Methoxytryptamines | |
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| Other ring subs. | |
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| α-Alkyltryptamines | |
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| Others | |
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- Ergolines/lysergamides (e.g., LSD)
- Ibogalogs (e.g., ibogainalog, tabernanthalog, Pharm-136)
- O-Methylnordehydrobufotenine
- Partial ergolines (e.g., NDTDI, RU-28306, CT-5252)
- Piperidinylethylindoles (e.g., pip-T)
- Pyrrolidinylethylindoles (e.g., pyr-T, 5-MeO-pyr-T)
- Pyrrolidinylmethylindoles (e.g., MPMI, 4-HO-MPMI (lucigenol), 5-MeO-MPMI, MSP-2020)
- Tetrahydropyridinylindoles (e.g., RU-28253 (5-MeO-THPI), NEtPhOH-THPI)
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- Others: 2C-B-AN
- 2C-DB
- 2C-G-x (e.g., 2C-G-3, 2C-G-5)
- β-Keto-2C-B (βk-2C-B)
- β-Keto-2C-I (βk-2C-I)
- β-Methyl-2C-B (BMB)
- (e.g., BOB, BOD, BOHB)
- (e.g., HOT-2, HOT-7, HOT-17)
- N-Ethyl-2C-B
- (e.g., 2CB-2-EtO, 2CD-2-EtO, 2CD-5-EtO, 2CE-5-EtO, 2CE-5iPrO, 2CT-5-EtO, 2CT2-2-EtO, 2CT7-2-EtO, ASR-2001 (2CB-5-PrO))
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| Others |
- 25B-NAcPip
- 2-DM-DOM
- 4-HA
- 5-DM-DOM
- Benzofurans (e.g., 5-APB, 5-APDB, 6-APB, 6-APDB, F, F-2, F-22)
- Benzothiophenes (e.g., 5-APBT, 6-APBT)
- BMB-202
- CT-5172
- DMAs (e.g., 2,4-DMA, 3,4-DMA)
- Fenfluramine
- MMA (3-MeO-4-MA)
- Norfenfluramine
- (e.g., 25D-NM-NDEAOP, DOB-NDEPA, DOI-NDEPA, DOM-NDEPA, DOTFM-NDEPA, M-NDEPA, TMA-2-NDEPA)
- PMA (4-MA)
- Thio-2Cs (e.g., 2C-5-TOET)
- Thio-DOx (e.g., 2-TOM, 5-TOET, 5-TOM, TOMSO)
- (e.g., TMA-3, TMA-4, TMA-5)
- ZDCM-04 (DOC-fenethylline)
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- 1-Aminomethylindanes (e.g., 2CB-Ind, jimscaline)
- 2-Aminoindanes (e.g., DOM-AI)
- 3-Benzazepines (e.g., lorcaserin)
- 3-Phenylpiperidines (e.g., LPH-5, LPH-48)
- Benzocyclobutenes (e.g., 2CBCB-NBOMe, TCB-2, tomscaline)
- Benzoxepins (e.g., BBOX, IBOX, TFMBOX)
- DMBMPP (juncosamine)
- Ergolines/lysergamides (e.g., LSD)
- Partial ergolines (e.g., NDTDI, DEIMDHPCA, DEMPDHPCA, DEMTMPDHPCA, DEMNDHPCA)
- Phenylcyclopropylamines (e.g., DMCPA, TMT)
- Phenyloxazolamines (aminorexes) (e.g., 2C-B-aminorex)
- Pyridopyrroloquinoxalines (e.g., IHCH-7113)
- Z3517967757
- ZC-B
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| Others |
- 9-Oxaergolines (e.g., RU-29717)
- γ-Carbolines (e.g., tiflucarbine)
- Arylpiperazines (e.g., 2C-B-PP, 2-NP, mCPP, MK-212, ORG-12962, pCPP, pFPP, quipazine, TFMPP, VCU-1012)
- Dihydrobenzoxazines (e.g., efavirenz)
- Phenoxyethylamines (e.g., CT-4719, ORG-37684)
- Pyridopyrroloquinoxalines (e.g., IHCH-7113)
- Quinazolinylethylamines (e.g., RH-34)
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| Natural sources |
- Tryptamines: Acacia spp. (e.g., Acacia acuminata, Acacia confusa)
- Ayahuasca and vinho de Jurema (e.g., Psychotria viridis (chacruna), Dipolopterys cabrerana (chaliponga, chacruna), Mimosa tenuiflora (Mimosa hostilis; jurema))
- Brosimum (e.g., Brosimum acutifolium (takini))
- Hallucinogenic snuffs (e.g., Anadenanthera peregrina (yopo, jopo, cohoba, parica, ebene), Anadenanthera colubrina (vilca, cebil))
- Incilius alvarius (Bufo alvarius; Colorado River toad, Sonoran Desert toad; bufo)
- Psilocybin-containing mushrooms (magic mushrooms, shrooms) (e.g., Psilocybe cubensis, Psilocybe mexicana (teonanacatl))
- Lysergamides: Achnatherum robustum (sleepy grass)
- Epichloë spp.
- Ergot (Claviceps) (e.g., Claviceps purpurea, Claviceps paspali)
- Morning glory (Convolvulaceae) seeds (e.g., Ipomoea tricolor (tlitliltzin, badoh negro; Ipomoea violacea), Ipomoea corymbosa (coaxihuitl, ololiúqui; Rivea Corymbosa, Turbina Corymbosa), Argyreia nervosa (Hawaiian baby woodrose; HBWR))
- Periglandula spp. (e.g., Periglandula ipomoeae, Periglandula clandestina)
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| Phenethylamines | |
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| Amphetamines | |
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| Phentermines | |
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| Cathinones | |
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Phenylisobutylamines
(and further-extended) | |
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Catecholamines
(and close relatives) | |
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Cyclized
phenethylamines | | Phenylalkylpyrrolidines | |
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2-Benzylpiperidines
(phenidates) | |
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Phenylmorpholines
(phenmetrazines) | |
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Phenyloxazolamines
(aminorexes) | |
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Isoquinolines and
tetrahydroisoquinolines | |
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| 2-Aminoindanes | |
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| 2-Aminotetralins | |
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| Others / unsorted |
- 1-Aminomethylindanes (e.g., 2CB-Ind, AMMI, bromojimscaline, jimscaline)
- 2-ADN
- 2-Benzhydrylpyrrolidine
- 2C-B-5-hemiFLY-α6 (BNAP)
- 2C-B-PYR
- 2CBecca
- 2CB7
- 2CJP
- 2CLisaB
- 2CLisaH
- 3-Aminochromans (e.g., CT-5126, 5-MeO-DPAC, robalzotan, ebalzotan)
- 3-Benzazepines (e.g., fenoldopam, lorcaserin, 7-chlorolorcaserin, SCHEMBL5334361)
- 3-Benzhydrylmorpholine
- 3-Phenylpiperidines (e.g., 3-phenylpiperidine, 3-PPP, OSU-6162 (PNU-96391), LPH-5, LPH-48, 2C-B-3PIP, 2C-B-3PIP-NBOMe, 2C-B-3PIP-POMe, Z3517967757 (Z7757))
- 6-AB
- AL-1095
- Aminochromes (e.g., adrenochrome, adrenolutin)
- AMMT
- Benzocyclobutenes (e.g., 2CBCB-NBOMe, bromotomscaline, S33005, TCB-2, tomscaline)
- Benzoxepins (e.g., BBOX, IBOX, TFMBOX)
- Butyltolylquinuclidine
- Camfetamine
- Clausenamide
- Cypenamine (trans-2-phenylcyclopentylamine)
- Diphenidine
- Diphenylprolinol
- Ergolines (e.g., LSD)
- Fencamfamin
- GYKI-52895
- HDMP-29
- Ivabradine
- Methoxphenidine
- Methylmorphenate
- Milnacipran
- MT-45
- 2-Naphthylamine
- Org 6582
- Partial ergolines (e.g., NDTDI, RU-27849, DEIMDHPCA, DEMPDHPCA, DEMPDHPCA-2C-D, RU-27251)
- PF-592,379
- Phenanthrenes (e.g., atherosperminine (atherospermine))
- Phenylcyclopropylamines (e.g., DMCPA, TMT, tranylcypromine)
- Phenylmethylpyrrolidines (e.g., APA-01)
- Phenylpiracetams (e.g., phenylpiracetam, MRZ-9547, RGPU-95)
- Pyridopyrroloquinoxalines (e.g., lumateperone, deulumateperone, IHCH-7079, IHCH-7086, IHCH-7113, ITI-1549)
- Thienopyridines (e.g., SKF-89145, SKF-89615, SKF-89626)
- Tolazoline
- Tricyclics (e.g., AMDA, AMDH, benzoctamine, dizocilpine, SpAMDA)
- ZC-B
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| Related compounds |
- 2-Furylethylamine
- 2-Pyrrolylethylamine
- 3-Pyrrolylethylamine
- 3-Pyrrolylpropylamine
- 2-Tetrahydrofurylethylamine
- 4-Benzylpiperidine
- 7-AB
- Alkylamines (e.g., 1,3-DMBATooltip 1,3-dimethylbutylamine, 1,4-DMAATooltip 1,4-dimethylamylamine, heptaminol, iproheptine, isometheptene, methylhexanamine/1,3-DMAA, octodrine, oenethyl, tuaminoheptane)
- Benzylamines (e.g., benzylamine, α-methylbenzylamine, MDM1EA, ALPHA, M-ALPHA, pargyline)
- Benzylpiperazines (e.g., benzylpiperazine, MDBZP, fipexide)
- Cyclohexylaminopropanes (e.g., propylhexedrine, norpropylhexedrine)
- Cyclopentylaminopropanes (e.g., isocyclamine, cyclopentamine)
- Phenoxyethylamines (e.g., 3,4,5-trimethoxyphenoxyethylamine, CT-4719, ORG-37684)
- Phenylalkenylamines (e.g., phenylbutenamine)
- Phenylalkynylamines (e.g., phenylbutynamine)
- Phenylpiperazines (e.g., 1-phenylpiperazine, mCPPTooltip meta-chlorophenylpiperazine, TFMPPTooltip trifluoromethylphenylpiperazine, oMPPTooltip ortho-methylphenylpiperazine, pFPPTooltip para-fluorophenylpiperazine, pMeOPPTooltip para-methoxyphenylpiperazine)
- Phenylpropylamines (e.g., phenylpropylamine, homo-MDA, homo-MDMA)
- Thienylaminopropanes (thiopropamines) (e.g., thiopropamine, methiopropamine, thiothinone)
- Phenylbutylamines (e.g., 4-Phenylbutylamine, 4-Phenylpentan-1-amine)
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