4-Methoxyamphetamine
Identification
- Name
- 4-Methoxyamphetamine
- Accession Number
- DB01472
- Description
- Not Available
- Type
- Small Molecule
- Groups
- Experimental, Illicit
- Structure
Structure for 4-Methoxyamphetamine (DB01472)
- Weight
- Average: 165.2322
Monoisotopic: 165.115364107 - Chemical Formula
- C10H15NO
- Synonyms
- (2RS)-1-(4-methoxyphenyl)propan-2-amine
- 4-methoxyamfetamine
- D,L-p-methoxyamphetamine
- Formoterol fumarate related compound G
- P-methoxyamfetamine
- P-methoxyamphetamine
- Paramethoxyamphetamine
- External IDs
- J213.549C
- J434.573H
Pharmacology
- Indication
- Not Available
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
- Not Available
- Mechanism of action
4-Methoxyamphetamine is a seratogenic drug of the amphetamine class. The drug acts as a potent and selective serotonin releasing agent. It binds to alpha receptors to mediate these effects.
Target Actions Organism ASodium-dependent dopamine transporter inhibitorHumans ASodium-dependent serotonin transporter inhibitorHumans ASynaptic vesicular amine transporter inhibitorHumans AAlpha-1A adrenergic receptor agonistHumans AAlpha-2A adrenergic receptor agonistHumans UAmine oxidase [flavin-containing] A inhibitorHumans UAmine oxidase [flavin-containing] B 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
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- 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 Unlock Additional DataAbatacept The metabolism of 4-Methoxyamphetamine can be increased when combined with Abatacept. Abiraterone The metabolism of 4-Methoxyamphetamine can be decreased when combined with Abiraterone. Acebutolol The therapeutic efficacy of 4-Methoxyamphetamine can be decreased when used in combination with Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when 4-Methoxyamphetamine is combined with Aceclofenac. Acemetacin The risk or severity of hypertension can be increased when 4-Methoxyamphetamine is combined with Acemetacin. Acetaminophen The metabolism of 4-Methoxyamphetamine can be decreased when combined with Acetaminophen. Acetazolamide The risk or severity of adverse effects can be increased when Acetazolamide is combined with 4-Methoxyamphetamine. Acetophenazine The risk or severity of adverse effects can be increased when Acetophenazine is combined with 4-Methoxyamphetamine. Acetylsalicylic acid The risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with 4-Methoxyamphetamine. Aclidinium 4-Methoxyamphetamine may increase the central nervous system depressant (CNS depressant) activities of Aclidinium. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
Products
Categories
- Drug Categories
- Adrenergic Agonists
- Adrenergic alpha-1 Receptor Agonists
- Adrenergic alpha-Agonists
- Agents producing tachycardia
- Agents that produce hypertension
- Amines
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 Substrates
- Ethylamines
- Hallucinogens
- Monoamine Oxidase A Inhibitors for interaction with Monoamine Oxidase A substrates
- Phenethylamines
- Psychotropic Drugs
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Phenethylamines
- Direct Parent
- Amphetamines and derivatives
- Alternative Parents
- Phenylpropanes / Phenoxy compounds / Methoxybenzenes / Anisoles / Aralkylamines / Alkyl aryl ethers / Organopnictogen compounds / Monoalkylamines / Hydrocarbon derivatives
- Substituents
- Alkyl aryl ether / Amine / Amphetamine or derivatives / Anisole / Aralkylamine / Aromatic homomonocyclic compound / Ether / Hydrocarbon derivative / Methoxybenzene / Organic nitrogen compound
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
Chemical Identifiers
- UNII
- OVB8F8P39Q
- CAS number
- 64-13-1
- InChI Key
- NEGYEDYHPHMHGK-UHFFFAOYSA-N
- InChI
- InChI=1S/C10H15NO/c1-8(11)7-9-3-5-10(12-2)6-4-9/h3-6,8H,7,11H2,1-2H3
- IUPAC Name
- 1-(4-methoxyphenyl)propan-2-amine
- SMILES
- COC1=CC=C(CC(C)N)C=C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 31721
- PubChem Substance
- 46507471
- ChemSpider
- 29417
- BindingDB
- 50024209
- ChEMBL
- CHEMBL278663
- Wikipedia
- 4-Methoxyamphetamine
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.928 mg/mL ALOGPS logP 1.74 ALOGPS logP 1.65 ChemAxon logS -2.2 ALOGPS pKa (Strongest Basic) 10.04 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 35.25 Å2 ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 50.17 m3·mol-1 ChemAxon Polarizability 19.29 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9971 Blood Brain Barrier + 0.9283 Caco-2 permeable + 0.7646 P-glycoprotein substrate Non-substrate 0.688 P-glycoprotein inhibitor I Non-inhibitor 0.9424 P-glycoprotein inhibitor II Non-inhibitor 0.9812 Renal organic cation transporter Non-inhibitor 0.7678 CYP450 2C9 substrate Non-substrate 0.8422 CYP450 2D6 substrate Substrate 0.8336 CYP450 3A4 substrate Non-substrate 0.6008 CYP450 1A2 substrate Inhibitor 0.6567 CYP450 2C9 inhibitor Non-inhibitor 0.9747 CYP450 2D6 inhibitor Inhibitor 0.8492 CYP450 2C19 inhibitor Non-inhibitor 0.6537 CYP450 3A4 inhibitor Non-inhibitor 0.9431 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8424 Ames test Non AMES toxic 0.6201 Carcinogenicity Non-carcinogens 0.8044 Biodegradation Not ready biodegradable 0.875 Rat acute toxicity 2.8848 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8836 hERG inhibition (predictor II) Non-inhibitor 0.8576
Spectra
- Mass Spec (NIST)
- Download (8.19 KB)
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Monoamine transmembrane transporter activity
- Specific Function
- Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
- Gene Name
- SLC6A3
- Uniprot ID
- Q01959
- Uniprot Name
- Sodium-dependent dopamine transporter
- Molecular Weight
- 68494.255 Da
References
- Daws LC, Irvine RJ, Callaghan PD, Toop NP, White JM, Bochner F: Differential behavioural and neurochemical effects of para-methoxyamphetamine and 3,4-methylenedioxymethamphetamine in the rat. Prog Neuropsychopharmacol Biol Psychiatry. 2000 Aug;24(6):955-77. [PubMed:11041537]
- Hansen JP, Riddle EL, Sandoval V, Brown JM, Gibb JW, Hanson GR, Fleckenstein AE: Methylenedioxymethamphetamine decreases plasmalemmal and vesicular dopamine transport: mechanisms and implications for neurotoxicity. J Pharmacol Exp Ther. 2002 Mar;300(3):1093-100. [PubMed:11861820]
- Fitzgerald JL, Reid JJ: Effects of methylenedioxymethamphetamine on the release of monoamines from rat brain slices. Eur J Pharmacol. 1990 Nov 27;191(2):217-20. [PubMed:1982265]
- Fleckenstein AE, Volz TJ, Riddle EL, Gibb JW, Hanson GR: New insights into the mechanism of action of amphetamines. Annu Rev Pharmacol Toxicol. 2007;47:681-98. [PubMed:17209801]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Serotonin:sodium symporter activity
- Specific Function
- Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into t...
- Gene Name
- SLC6A4
- Uniprot ID
- P31645
- Uniprot Name
- Sodium-dependent serotonin transporter
- Molecular Weight
- 70324.165 Da
References
- Daws LC, Irvine RJ, Callaghan PD, Toop NP, White JM, Bochner F: Differential behavioural and neurochemical effects of para-methoxyamphetamine and 3,4-methylenedioxymethamphetamine in the rat. Prog Neuropsychopharmacol Biol Psychiatry. 2000 Aug;24(6):955-77. [PubMed:11041537]
- Shankaran M, Yamamoto BK, Gudelsky GA: Involvement of the serotonin transporter in the formation of hydroxyl radicals induced by 3,4-methylenedioxymethamphetamine. Eur J Pharmacol. 1999 Dec 3;385(2-3):103-10. [PubMed:10607865]
- Whitworth TL, Herndon LC, Quick MW: Psychostimulants differentially regulate serotonin transporter expression in thalamocortical neurons. J Neurosci. 2002 Jan 1;22(1):RC192. [PubMed:11756522]
- Szabo Z, McCann UD, Wilson AA, Scheffel U, Owonikoko T, Mathews WB, Ravert HT, Hilton J, Dannals RF, Ricaurte GA: Comparison of (+)-(11)C-McN5652 and (11)C-DASB as serotonin transporter radioligands under various experimental conditions. J Nucl Med. 2002 May;43(5):678-92. [PubMed:11994534]
- Boot BP, Mechan AO, McCann UD, Ricaurte GA: MDMA- and p-chlorophenylalanine-induced reduction in 5-HT concentrations: effects on serotonin transporter densities. Eur J Pharmacol. 2002 Oct 25;453(2-3):239-44. [PubMed:12398910]
- Saldana SN, Barker EL: Temperature and 3,4-methylenedioxymethamphetamine alter human serotonin transporter-mediated dopamine uptake. Neurosci Lett. 2004 Jan 16;354(3):209-12. [PubMed:14700733]
- Bogen IL, Haug KH, Myhre O, Fonnum F: Short- and long-term effects of MDMA ("ecstasy") on synaptosomal and vesicular uptake of neurotransmitters in vitro and ex vivo. Neurochem Int. 2003 Sep-Oct;43(4-5):393-400. [PubMed:12742084]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Monoamine transmembrane transporter activity
- Specific Function
- Involved in the ATP-dependent vesicular transport of biogenic amine neurotransmitters. Pumps cytosolic monoamines including dopamine, norepinephrine, serotonin, and histamine into synaptic vesicles...
- Gene Name
- SLC18A2
- Uniprot ID
- Q05940
- Uniprot Name
- Synaptic vesicular amine transporter
- Molecular Weight
- 55712.075 Da
References
- Biezonski DK, Meyer JS: Effects of 3,4-methylenedioxymethamphetamine (MDMA) on serotonin transporter and vesicular monoamine transporter 2 protein and gene expression in rats: implications for MDMA neurotoxicity. J Neurochem. 2010 Feb;112(4):951-62. doi: 10.1111/j.1471-4159.2009.06515.x. Epub 2009 Nov 30. [PubMed:20002520]
- Hansen JP, Riddle EL, Sandoval V, Brown JM, Gibb JW, Hanson GR, Fleckenstein AE: Methylenedioxymethamphetamine decreases plasmalemmal and vesicular dopamine transport: mechanisms and implications for neurotoxicity. J Pharmacol Exp Ther. 2002 Mar;300(3):1093-100. [PubMed:11861820]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Protein heterodimerization activity
- Specific Function
- This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
- Gene Name
- ADRA1A
- Uniprot ID
- P35348
- Uniprot Name
- Alpha-1A adrenergic receptor
- Molecular Weight
- 51486.005 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Thioesterase binding
- Specific Function
- Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
- Gene Name
- ADRA2A
- Uniprot ID
- P08913
- Uniprot Name
- Alpha-2A adrenergic receptor
- Molecular Weight
- 48956.275 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Serotonin binding
- Specific Function
- Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
- Gene Name
- MAOA
- Uniprot ID
- P21397
- Uniprot Name
- Amine oxidase [flavin-containing] A
- Molecular Weight
- 59681.27 Da
References
- Green AL, El Hait MA: p-Methoxyamphetamine, a potent reversible inhibitor of type-A monoamine oxidase in vitro and in vivo. J Pharm Pharmacol. 1980 Apr;32(4):262-6. [PubMed:6103055]
- Ask AL, Fagervall I, Ross SB: Selective inhibition of monoamine oxidase in monoaminergic neurons in the rat brain. Naunyn Schmiedebergs Arch Pharmacol. 1983 Sep;324(2):79-87. [PubMed:6646243]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Primary amine oxidase activity
- Specific Function
- Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
- Gene Name
- MAOB
- Uniprot ID
- P27338
- Uniprot Name
- Amine oxidase [flavin-containing] B
- Molecular Weight
- 58762.475 Da
References
- Green AL, El Hait MA: p-Methoxyamphetamine, a potent reversible inhibitor of type-A monoamine oxidase in vitro and in vivo. J Pharm Pharmacol. 1980 Apr;32(4):262-6. [PubMed:6103055]
- Ask AL, Fagervall I, Ross SB: Selective inhibition of monoamine oxidase in monoaminergic neurons in the rat brain. Naunyn Schmiedebergs Arch Pharmacol. 1983 Sep;324(2):79-87. [PubMed:6646243]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Wu D, Otton SV, Inaba T, Kalow W, Sellers EM: Interactions of amphetamine analogs with human liver CYP2D6. Biochem Pharmacol. 1997 Jun 1;53(11):1605-12. [PubMed:9264312]
- Flockhart Table of Drug Interactions [Link]
Drug created on June 13, 2005 07:24 / Updated on June 12, 2020 10:51
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