Identification

Generic Name
Tenamfetamine
DrugBank Accession Number
DB01509
Background

An amphetamine derivative that inhibits uptake of catecholamine neurotransmitters. It is a hallucinogen. It is less toxic than its methylated derivative but in sufficient doses may still destroy serotonergic neurons and has been used for that purpose experimentally. [PubChem]

Type
Small Molecule
Groups
Experimental, Illicit
Structure
Thumb
Weight
Average: 179.2157
Monoisotopic: 179.094628665
Chemical Formula
C10H13NO2
Synonyms
  • 3,4-methylenedioxyamphetamine
  • MDA
  • Methylenedioxyamphetamine
  • Tenamfetamina
  • Tenamfetamine
  • Tenamfetaminum
External IDs
  • EA-1299
  • SKF-5

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
Improve clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events & improve clinical decision support.
Learn more
Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Adverseeffects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.
Learn more
Improve decision support & research outcomes with our structured adverse effects data.
Learn more
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Tenamfetamine is combined with 1,2-Benzodiazepine.
AbaloparatideThe risk or severity of adverse effects can be increased when Tenamfetamine is combined with Abaloparatide.
AcebutololThe therapeutic efficacy of Acebutolol can be decreased when used in combination with Tenamfetamine.
AceclofenacThe risk or severity of hypertension can be increased when Tenamfetamine is combined with Aceclofenac.
AcemetacinThe risk or severity of hypertension can be increased when Tenamfetamine is combined with Acemetacin.
AcenocoumarolThe risk or severity of adverse effects can be increased when Tenamfetamine is combined with Acenocoumarol.
AcetazolamideAcetazolamide may decrease the excretion rate of Tenamfetamine which could result in a higher serum level.
AcetophenazineThe risk or severity of adverse effects can be increased when Tenamfetamine is combined with Acetophenazine.
Acetylsalicylic acidThe risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Tenamfetamine.
AclidiniumTenamfetamine may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
Interactions
Identify potential medication risks
Easily compare up to 40 drugs with our drug interaction checker.
Get severity rating, description, and management advice.
Learn more
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzodioxoles
Sub Class
Not Available
Direct Parent
Benzodioxoles
Alternative Parents
Aralkylamines / Benzenoids / Oxacyclic compounds / Acetals / Organopnictogen compounds / Monoalkylamines / Hydrocarbon derivatives
Substituents
Acetal / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Benzenoid / Benzodioxole / Hydrocarbon derivative / Organic nitrogen compound / Organic oxygen compound / Organonitrogen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
XJZ28FJ27W
CAS number
4764-17-4
InChI Key
NGBBVGZWCFBOGO-UHFFFAOYSA-N
InChI
InChI=1S/C10H13NO2/c1-7(11)4-8-2-3-9-10(5-8)13-6-12-9/h2-3,5,7H,4,6,11H2,1H3
IUPAC Name
1-(2H-1,3-benzodioxol-5-yl)propan-2-amine
SMILES
CC(N)CC1=CC2=C(OCO2)C=C1

References

General References
Not Available
Human Metabolome Database
HMDB0041931
PubChem Compound
1614
PubChem Substance
46506100
ChemSpider
1555
BindingDB
50005247
ChEBI
100592
ChEMBL
CHEMBL6731
Wikipedia
3,4-Methylenedioxyamphetamine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Not Yet RecruitingBasic ScienceHealthy Subjects (HS)1
Not AvailableCompletedBasic ScienceHealthy Subjects (HS)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP1.64HANSCH,C & LEO,AJ (1985)
pKa9.67 (at 25 °C)PERRIN,DD (1965)
Predicted Properties
PropertyValueSource
Water Solubility2.83 mg/mLALOGPS
logP1.15ALOGPS
logP1.43ChemAxon
logS-1.8ALOGPS
pKa (Strongest Basic)10.01ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area44.48 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity49.47 m3·mol-1ChemAxon
Polarizability19.51 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9668
Caco-2 permeable+0.6011
P-glycoprotein substrateNon-substrate0.7169
P-glycoprotein inhibitor INon-inhibitor0.9117
P-glycoprotein inhibitor IINon-inhibitor0.9278
Renal organic cation transporterNon-inhibitor0.801
CYP450 2C9 substrateNon-substrate0.8661
CYP450 2D6 substrateNon-substrate0.6198
CYP450 3A4 substrateNon-substrate0.6464
CYP450 1A2 substrateInhibitor0.7625
CYP450 2C9 inhibitorNon-inhibitor0.8247
CYP450 2D6 inhibitorInhibitor0.7713
CYP450 2C19 inhibitorNon-inhibitor0.5475
CYP450 3A4 inhibitorNon-inhibitor0.7028
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5
Ames testNon AMES toxic0.6835
CarcinogenicityNon-carcinogens0.8578
BiodegradationReady biodegradable0.6509
Rat acute toxicity2.4882 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9589
hERG inhibition (predictor II)Non-inhibitor0.9386
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0900000000-ceb833ad1eb42d11bf4a
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0900000000-7795b35d40550ca1ea10
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03ei-0900000000-510f32fec3a45da3afe8
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a5i-0900000000-5ba589950b29c036e6af
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4r-2900000000-7d9cec73d2dd144096d7
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a6r-4900000000-56ce80af24db379bcf90
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0fb9-9500000000-7c78e7d8dc85b9c6aa0d
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0fba-9200000000-9b312e42e8f1bd38d687
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-9100000000-38f4dd19df31aa785f14

Drug created at July 31, 2007 13:10 / Updated at February 21, 2021 18:51