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Chemical compound
Pharmaceutical compound
N -t -BOC-MDMAOther names NBoc-MDMA; NB-MDMA; N -tert -Butoxycarbonyl-3,4-methylenedioxymethamphetamine; N -tert -Butoxycarbonyl-MDMA
tert -Butyl N -[1-(1,3-benzodioxol-5-yl)propan-2-yl]-N -methylcarbamate
CAS Number PubChem CID ChemSpider UNII Formula C 16 H 23 N O 4 Molar mass −1 3D model (JSmol )
CC(CC1=CC2=C(C=C1)OCO2)N(C)C(=O)OC(C)(C)C
InChI=1S/C16H23NO4/c1-11(17(5)15(18)21-16(2,3)4)8-12-6-7-13-14(9-12)20-10-19-13/h6-7,9,11H,8,10H2,1-5H3
Key:AXMVJRRNQRXHMX-UHFFFAOYSA-N
N -t -BOC-MDMAN -tert -butoxycarbonyl-MDMAchemical compound which can be both a synthetic precursor to, or a prodrug of the entactogenic drug MDMA ("ecstasy"). It was first identified in Australia in 2015 as a seizure by customs, and has subsequently been found in China , the Netherlands and other European countries. Originally it was thought to be intended as a non-illegal form of MDMA which could be easily converted into the prohibited final product after importation, however one seizure by police found N -t -BOC-MDMA in the process of being pressed into pills, and experiments with simulated gastric fluid confirmed that it can be broken down to MDMA by human stomach acid. Similar N -protectedN -t -BOC-methamphetamine, N -p -tosyl-methamphetamine, N -t -BOC-ketamine, N -t -BOC-norketamine, and N -methoxycarbonyl-MDA have also been encountered by law enforcement.[ 1] [ 2] [ 3] [ 4] [ 5] [ 6] [ 7]
Chemical structures of N -t -BOC-methamphetamine, N -p -tosyl-methamphetamine, N -t -BOC-ketamine, and N -methoxycarbonyl-MDA
Society and culture [ edit ] N -t -BOC-MDMA has been specifically listed as an illicit drug in Singapore and South Korea,[ 8] [ 9]
N -t -BOC-MDMA is controlled substance in Canada under phenethylamine blanket-ban language.[ 10]
N -t -BOC-MDMA is not an explicitly controlled substance in the United States .[ 11] Federal Analogue Act if intended for human consumption.
^ Collins M, Donnelly C, Cameron S, Tahtouh M, Salouros H (March 2017). "Identification and characterization of N-tert-butoxycarbonyl-MDMA: a new MDMA precursor". Drug Testing and Analysis . 9 (3): 399– 404. doi :10.1002/dta.2059 . PMID 27574107 . ^ Sugie KI, Kurakami D, Akutsu M, Saito K (2018). "Rapid detection of tert-butoxycarbonyl-methamphetamine by direct analysis in real time time-of-flight mass spectrometry" . Forensic Toxicology . 36 (2): 261– 269. doi :10.1007/s11419-017-0400-y . PMC 6002434 PMID 29963202 . ^ Salouros H (2018). "Illicit drug chemical profiling: current and future state". Australian Journal of Forensic Sciences . 50 (6): 689– 696. doi :10.1080/00450618.2018.1424244 . S2CID 80559699 . ^ Collins M, Bhattarai A, Salouros H (2018). "Another chemically masked drug: p-tosyl methylamphetamine". Drug Testing and Analysis . 10 (5): 898– 905. doi :10.1002/dta.2363 . PMID 29388381 . ^ Johnson CS, Bogun B (2019). "Chemical camouflage: illicit drug concealment using di-tert-butyldicarbonate". Australian Journal of Forensic Sciences . 51 : S217– S219. doi :10.1080/00450618.2019.1569135 . S2CID 86747489 . ^ European Monitoring Centre for Drugs and Drug Addiction (2019). "Drug precursor developments in the European Union" (PDF) . EMCDDA Papers . Luxembourg: Publications Office of the European Union. ^ "Prosecutors Detail 500 Kilogram Ketamine Precursor Raid" . ICRT.com . 3 March 2020.^ "Singapore Misuse of Drugs (Amendment No. 2) Regulations 2020" .^ "Han-soo L. Ministry lists 10 substances on temporary narcotics list" . Korea Biomedical Review . 11 May 2018.^ "Controlled Drugs and Substances Act" . Department of Justice Canada . 5 December 2025. Retrieved 20 January 2026 .^ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF) , United States : U.S. Department of Justice : Drug Enforcement Administration (DEA): Diversion Control Division, January 2026
No ring subs. 4-Hydroxytryptamines 5-Hydroxytryptamines 5-Methoxytryptamines Other ring subs. α-Alkyltryptamines Others
Ergolines /lysergamides (e.g., LSD )Ibogalogs (e.g., ibogainalog , tabernanthalog , Pharm-136 )O -MethylnordehydrobufoteninePartial 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 )
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) BOB , BOD , BOHB )HOT-2 , HOT-7 , HOT-17 )N -Ethyl-2C-B2CB-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) ) 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 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 )TMA-3 , TMA-4 , TMA-5 )ZDCM-04 (DOC-fenethylline)
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
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 ) Natural sources
Tryptamines: Acacia spp.Acacia acuminata Acacia confusa Ayahuasca and vinho de Jurema (e.g., Psychotria viridis (chacruna)Dipolopterys cabrerana (chaliponga, chacruna)Mimosa tenuiflora (Mimosa hostilis ; jurema)Brosimum 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.Periglandula ipomoeae Periglandula clandestina
DRAs Tooltip Dopamine releasing agents
NRAs Tooltip Norepinephrine releasing agents
SRAs Tooltip Serotonin releasing agents
Others
Phenethylamines Amphetamines Phentermines Cathinones Phenylisobutylamines (and further-extended) Catecholamines (and close relatives) Cyclized
Phenylalkylpyrrolidines 2-Benzylpiperidines (phenidates ) Phenylmorpholines (phenmetrazines) Phenyloxazolamines (aminorexes) Isoquinolines andtetrahydroisoquinolines 2-Aminoindanes 2-Aminotetralins 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 )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
Related compounds
2-Furylethylamine 2-Pyrrolylethylamine 3-Pyrrolylethylamine 3-Pyrrolylpropylamine 2-Tetrahydrofurylethylamine 4-Benzylpiperidine 7-AB Alkylamines (e.g., 1,3-DMBA Tooltip 1,3-dimethylbutylamine , 1,4-DMAA Tooltip 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 , mCPP Tooltip meta-chlorophenylpiperazine , TFMPP Tooltip trifluoromethylphenylpiperazine , oMPP Tooltip ortho-methylphenylpiperazine , pFPP Tooltip para-fluorophenylpiperazine , pMeOPP Tooltip 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 )
