3,4-Methylenedioxyphentermine

3,4-Methylenedioxyphentermine
Names
	Preferred IUPAC name 1-(2H-1,3-Benzodioxol-5-yl)-2-methylpropan-2-amine
	Other names MDP; MDPH; 3,4-Methylenedioxyphentermine;; 3,4-Methylenedioxy-alpha,alpha-dimethyl-1-ethane
Identifiers
CAS Number	39235-63-7 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL126226;
ChemSpider	15204207 ;
PubChem CID	13020598;
UNII	WF9K2PM8J8;
CompTox Dashboard (EPA)	DTXSID90515395;
	InChI InChI=1S/C11H15NO2/c1-11(2,12)6-8-3-4-9-10(5-8)14-7-13-9/h3-5H,6-7,12H2,1-2H3 Key: OIZBHKBNZXRXSM-UHFFFAOYSA-N ; InChI=1/C11H15NO2/c1-11(2,12)6-8-3-4-9-10(5-8)14-7-13-9/h3-5H,6-7,12H2,1-2H3 Key: OIZBHKBNZXRXSM-UHFFFAOYAY;
	SMILES NC(C)(C)CC1=CC(OCO2)=C2C=C1;
Properties
Chemical formula	C11H15NO2
Molar mass	193.246 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

3,4-Methylenedioxyphentermine (MDPH) is a lesser-known drug of the amphetamine family. MDPH was first synthesized by Alexander Shulgin. Very little data exists about the pharmacological properties, metabolism, and toxicity of MDPH.

In his book PiHKAL (Phenethylamines i Have Known And Loved), the dosage range is listed as 160–240 mg, and the duration as 3–5 hours.^[1] MDPH's effects are very similar to those of MDA: they both are smooth and "stoning," and do not cause any visuals. They also alter dreams and dream patterns. Shulgin describes MDPH as a promoter; it promotes the effects of other drugs, similarly to 2C-D.

The N-methyl derivative, 3,4-methylenedioxy-N-methylphentermine (MDMPH), has been described by Shulgin as lacking MDMA-like effects.^[2] Accordingly, MDMPH, as well as MDPH, were found to be inactive as serotonin releasing agents in vitro.^[2]^[3]

Legality

United Kingdom

This substance is a Class A drug in the Drugs controlled by the UK Misuse of Drugs Act.^[4]

References

^ MDPH entry in PiHKAL
^ ^a ^b Nichols, David F.; Oberlender, Robert (1990). "Structure-Activity Relationships of MDMA and Related Compounds: A New Class of Psychoactive Agents?". Ecstasy: The Clinical, Pharmacological and Neurotoxicological Effects of the Drug MDMA. Vol. 9. Boston, MA: Springer US. p. 105–131. doi:10.1007/978-1-4613-1485-1_7. ISBN 978-1-4612-8799-5.
^ Nichols DE, Lloyd DH, Hoffman AJ, Nichols MB, Yim GK (May 1982). "Effects of certain hallucinogenic amphetamine analogues on the release of [3H]serotonin from rat brain synaptosomes". J Med Chem. 25 (5): 530–535. doi:10.1021/jm00347a010. PMID 7086839.
^ "UK Misuse of Drugs act 2001 Amendment summary". Isomer Design. Archived from the original on 22 October 2017. Retrieved 12 March 2014.

[1] MDPH entry in PiHKAL

[NicholsOberlender1990-2] Nichols, David F.; Oberlender, Robert (1990). "Structure-Activity Relationships of MDMA and Related Compounds: A New Class of Psychoactive Agents?". Ecstasy: The Clinical, Pharmacological and Neurotoxicological Effects of the Drug MDMA. Vol. 9. Boston, MA: Springer US. p. 105–131. doi:10.1007/978-1-4613-1485-1_7. ISBN 978-1-4612-8799-5.

[NicholsLloydHoffman1982-3] Nichols DE, Lloyd DH, Hoffman AJ, Nichols MB, Yim GK (May 1982). "Effects of certain hallucinogenic amphetamine analogues on the release of [3H]serotonin from rat brain synaptosomes". J Med Chem. 25 (5): 530–535. doi:10.1021/jm00347a010. PMID 7086839.

[4] "UK Misuse of Drugs act 2001 Amendment summary". Isomer Design. Archived from the original on 22 October 2017. Retrieved 12 March 2014.

[1]

[2]

[3]

[4]

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

Legality

United Kingdom

See also

References