Tenamfetamine
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Explore a selection of our essential drug information below, or:
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
- 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
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism ASodium-dependent noradrenaline transporter inhibitorHumans ASodium-dependent serotonin transporter inhibitorHumans ASodium-dependent dopamine transporter inhibitorHumans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Tenamfetamine is combined with 1,2-Benzodiazepine. Acebutolol The therapeutic efficacy of Acebutolol can be decreased when used in combination with Tenamfetamine. Aceclofenac The risk or severity of hypertension can be increased when Tenamfetamine is combined with Aceclofenac. Acemetacin The risk or severity of hypertension can be increased when Tenamfetamine is combined with Acemetacin. Acenocoumarol The risk or severity of adverse effects can be increased when Tenamfetamine is combined with Acenocoumarol. - Food Interactions
- Not Available
Categories
- Drug Categories
- Adrenergic Agents
- Adrenergic Uptake Inhibitors
- Agents producing tachycardia
- Agents that produce hypertension
- Amines
- Amphetamines
- Antidepressive Agents
- Central Nervous System Agents
- Central Nervous System Depressants
- Ethylamines
- Hallucinogens
- Membrane Transport Modulators
- Neurotransmitter Agents
- Neurotransmitter Uptake Inhibitors
- Phenethylamines
- Psychotropic Drugs
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Serotonin Agents
- Serotonin Modulators
- Sympathomimetics
- 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
- External Links
- 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
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Basic Science Healthy Volunteers (HV) 1 somestatus stop reason just information to hide 1 Completed Basic Science Healthy Volunteers (HV) 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 1.64 HANSCH,C & LEO,AJ (1985) pKa 9.67 (at 25 °C) PERRIN,DD (1965) - Predicted Properties
Property Value Source Water Solubility 2.83 mg/mL ALOGPS logP 1.15 ALOGPS logP 1.43 Chemaxon logS -1.8 ALOGPS pKa (Strongest Basic) 10.01 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 44.48 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 49.47 m3·mol-1 Chemaxon Polarizability 19.5 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9668 Caco-2 permeable + 0.6011 P-glycoprotein substrate Non-substrate 0.7169 P-glycoprotein inhibitor I Non-inhibitor 0.9117 P-glycoprotein inhibitor II Non-inhibitor 0.9278 Renal organic cation transporter Non-inhibitor 0.801 CYP450 2C9 substrate Non-substrate 0.8661 CYP450 2D6 substrate Non-substrate 0.6198 CYP450 3A4 substrate Non-substrate 0.6464 CYP450 1A2 substrate Inhibitor 0.7625 CYP450 2C9 inhibitor Non-inhibitor 0.8247 CYP450 2D6 inhibitor Inhibitor 0.7713 CYP450 2C19 inhibitor Non-inhibitor 0.5475 CYP450 3A4 inhibitor Non-inhibitor 0.7028 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5 Ames test Non AMES toxic 0.6835 Carcinogenicity Non-carcinogens 0.8578 Biodegradation Ready biodegradable 0.6509 Rat acute toxicity 2.4882 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9589 hERG inhibition (predictor II) Non-inhibitor 0.9386
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 144.6351959 predictedDarkChem Lite v0.1.0 [M-H]- 135.90797 predictedDeepCCS 1.0 (2019) [M+H]+ 145.3612959 predictedDarkChem Lite v0.1.0 [M+H]+ 138.71764 predictedDeepCCS 1.0 (2019) [M+Na]+ 144.8274959 predictedDarkChem Lite v0.1.0 [M+Na]+ 147.92368 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Mediates sodium- and chloride-dependent transport of norepinephrine (also known as noradrenaline) (PubMed:2008212, PubMed:8125921). Can also mediate sodium- and chloride-dependent transport of dopamine (PubMed:11093780, PubMed:8125921)
- Specific Function
- actin binding
- Gene Name
- SLC6A2
- Uniprot ID
- P23975
- Uniprot Name
- Sodium-dependent noradrenaline transporter
- Molecular Weight
- 69331.42 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
2. DetailsSodium-dependent serotonin transporter
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Serotonin transporter that cotransports serotonin with one Na(+) ion in exchange for one K(+) ion and possibly one proton in an overall electroneutral transport cycle. Transports serotonin across the plasma membrane from the extracellular compartment to the cytosol thus limiting serotonin intercellular signaling (PubMed:10407194, PubMed:12869649, PubMed:21730057, PubMed:27049939, PubMed:27756841, PubMed:34851672). Essential for serotonin homeostasis in the central nervous system. In the developing somatosensory cortex, acts in glutamatergic neurons to control serotonin uptake and its trophic functions accounting for proper spatial organization of cortical neurons and elaboration of sensory circuits. In the mature cortex, acts primarily in brainstem raphe neurons to mediate serotonin uptake from the synaptic cleft back into the pre-synaptic terminal thus terminating serotonin signaling at the synapse (By similarity). Modulates mucosal serotonin levels in the gastrointestinal tract through uptake and clearance of serotonin in enterocytes. Required for enteric neurogenesis and gastrointestinal reflexes (By similarity). Regulates blood serotonin levels by ensuring rapid high affinity uptake of serotonin from plasma to platelets, where it is further stored in dense granules via vesicular monoamine transporters and then released upon stimulation (PubMed:17506858, PubMed:18317590). Mechanistically, the transport cycle starts with an outward-open conformation having Na1(+) and Cl(-) sites occupied. The binding of a second extracellular Na2(+) ion and serotonin substrate leads to structural changes to outward-occluded to inward-occluded to inward-open, where the Na2(+) ion and serotonin are released into the cytosol. Binding of intracellular K(+) ion induces conformational transitions to inward-occluded to outward-open and completes the cycle by releasing K(+) possibly together with a proton bound to Asp-98 into the extracellular compartment. Na1(+) and Cl(-) ions remain bound throughout the transport cycle (PubMed:10407194, PubMed:12869649, PubMed:21730057, PubMed:27049939, PubMed:27756841, PubMed:34851672). Additionally, displays serotonin-induced channel-like conductance for monovalent cations, mainly Na(+) ions. The channel activity is uncoupled from the transport cycle and may contribute to the membrane resting potential or excitability (By similarity)
- Specific Function
- actin filament binding
- Gene Name
- SLC6A4
- Uniprot ID
- P31645
- Uniprot Name
- Sodium-dependent serotonin transporter
- Molecular Weight
- 70324.165 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
3. DetailsSodium-dependent dopamine transporter
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Mediates sodium- and chloride-dependent transport of dopamine (PubMed:10375632, PubMed:11093780, PubMed:1406597, PubMed:15505207, PubMed:19478460, PubMed:8302271). Also mediates sodium- and chloride-dependent transport of norepinephrine (also known as noradrenaline) (By similarity). Regulator of light-dependent retinal hyaloid vessel regression, downstream of OPN5 signaling (By similarity)
- Specific Function
- amine binding
- Gene Name
- SLC6A3
- Uniprot ID
- Q01959
- Uniprot Name
- Sodium-dependent dopamine transporter
- Molecular Weight
- 68494.255 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at July 31, 2007 13:10 / Updated at August 26, 2024 19:22