Drug Information

Drug General Information
Drug ID
D0B5OI
Former ID
DNC003316
Drug Name
4-Methoxyamphetamine
Drug Type
Small molecular drug
Indication Discovery agent Investigative [551380]
Structure
Download
2D MOL

3D MOL
Formula
C10H15NO
Canonical SMILES
CC(CC1=CC=C(C=C1)OC)N
InChI
1S/C10H15NO/c1-8(11)7-9-3-5-10(12-2)6-4-9/h3-6,8H,7,11H2,1-2H3
InChIKey
NEGYEDYHPHMHGK-UHFFFAOYSA-N
CAS Number
CAS 23239-32-9
PubChem Compound ID
31721
PubChem Substance ID
91153, 841175, 3249416, 4962210, 7962430, 8172362, 10514619, 11407235, 15194941, 29328496, 29535053, 34673826, 46507471, 50004572, 50113081, 56310714, 57311273, 77832186, 103180329, 103934500, 104311633, 117534770, 117854057, 118384425, 125567154, 125810021, 125812893, 126567610, 128689834, 128741831, 131818658, 134224394, 134351252, 134995452, 135022208, 137005596, 139244038, 143441114, 144024467, 160838603, 160964731, 162118404, 162889075, 163403525, 170539116, 172864323, 179680040, 204427290, 223893594, 226612410
Target and Pathway
Target(s) Alpha-2A adrenergic receptor Target Info Agonist [551380]
Synaptic vesicle amine transporter Target Info Antagonist [551380]
Alpha-1D adrenergic receptor Target Info Agonist [551380]
Amine oxidase [flavin-containing] B Target Info Antagonist [551380]
Amine oxidase [flavin-containing] A Target Info Antagonist [551380]
Sodium-dependent dopamine transporter Target Info Antagonist [551380]
Alpha-1A adrenergic receptor Target Info Agonist [551380]
Sodium-dependent serotonin transporter Target Info Antagonist [551380]
BioCyc Pathway Superpathway of tryptophan utilization
Tryptophan degradation via tryptamine
Dopamine degradation
Putrescine degradation III
Noradrenaline and adrenaline degradationPWY66-401:Superpathway of tryptophan utilization
Noradrenaline and adrenaline degradation
Serotonin degradation
Superpathway of melatonin degradation
Melatonin degradation II
KEGG Pathway cGMP-PKG signaling pathway
Neuroactive ligand-receptor interactionhsa04721:Synaptic vesicle cycle
Serotonergic synapse
Dopaminergic synapse
Parkinson's disease
Cocaine addiction
Amphetamine addiction
Alcoholismhsa04020:Calcium signaling pathway
Neuroactive ligand-receptor interaction
Adrenergic signaling in cardiomyocytes
Vascular smooth muscle contraction
Salivary secretionhsa00260:Glycine, serine and threonine metabolism
Arginine and proline metabolism
Histidine metabolism
Tyrosine metabolism
Phenylalanine metabolism
Tryptophan metabolism
Drug metabolism - cytochrome P450
Metabolic pathways
Alcoholismhsa00260:Glycine, serine and threonine metabolism
Alcoholismhsa04728:Dopaminergic synapse
AMPK signaling pathway
Salivary secretionhsa04726:Serotonergic synapse
NetPath Pathway IL2 Signaling PathwayNetPath_16:IL4 Signaling PathwayNetPath_11:TCR Signaling Pathway
PANTHER Pathway Alpha adrenergic receptor signaling pathwayP00001:Adrenaline and noradrenaline biosynthesis
5HT1 type receptor mediated signaling pathway
5HT2 type receptor mediated signaling pathway
5HT3 type receptor mediated signaling pathway
5HT4 type receptor mediated signaling pathway
Dopamine receptor mediated signaling pathway
Nicotine pharmacodynamics pathway
CCKR signaling map STP00001:Adrenaline and noradrenaline biosynthesis
5-Hydroxytryptamine degredation
Dopamine receptor mediated signaling pathwayP00001:Adrenaline and noradrenaline biosynthesis
Parkinson disease
Dopamine receptor mediated signaling pathwayP00002:Alpha adrenergic receptor signaling pathwayP04373:5HT1 type receptor mediated signaling pathway
Pathway Interaction Database Alpha-synuclein signalingalphasynuclein_pathway:Alpha-synuclein signaling
PathWhiz Pathway Histidine Metabolism
Tyrosine Metabolism
Glycine and Serine Metabolism
Reactome Adrenoceptors
Adrenaline signalling through Alpha-2 adrenergic receptor
Adrenaline,noradrenaline inhibits insulin secretion
G alpha (i) signalling events
G alpha (z) signalling events
Surfactant metabolismR-HSA-181430:Norepinephrine Neurotransmitter Release Cycle
Na+/Cl- dependent neurotransmitter transportersR-HSA-390696:Adrenoceptors
G alpha (q) signalling events
G alpha (12/13) signalling eventsR-HSA-181430:Norepinephrine Neurotransmitter Release CycleR-HSA-442660:Na+/Cl- dependent neurotransmitter transportersR-HSA-390696:Adrenoceptors
G alpha (12/13) signalling events
WikiPathways Monoamine GPCRs
GPCRs, Class A Rhodopsin-like
Platelet Aggregation (Plug Formation)
Integration of energy metabolism
GPCR ligand binding
GPCR downstream signalingWP2855:Dopaminergic Neurogenesis
Synaptic Vesicle Pathway
Neurotransmitter Release Cycle
Nicotine Activity on Dopaminergic NeuronsWP58:Monoamine GPCRs
Calcium Regulation in the Cardiac Cell
Gastrin-CREB signalling pathway via PKC and MAPK
GPCR downstream signaling
GPCRs, OtherWP465:Tryptophan metabolism
Dopamine metabolism
Phase 1 - Functionalization of compoundsWP706:SIDS Susceptibility Pathways
Biogenic Amine Synthesis
Oxidative Stress
Phase 1 - Functionalization of compounds
Neurotransmitter Clearance In The Synaptic Cleft
Serotonin Transporter ActivityWP727:Monoamine Transport
NRF2 pathway
Dopaminergic Neurogenesis
Parkinsons Disease Pathway
Transport of glucose and other sugars, bile salts and organic acids, metal ions and amine compounds
Neurotransmitter Clearance In The Synaptic CleftWP58:Monoamine GPCRs
Endothelin Pathways
AMPK SignalingWP727:Monoamine Transport
SIDS Susceptibility Pathways
Serotonin Transporter Activity
References
Ref 551380Differential behavioural and neurochemical effects of para-methoxyamphetamine and 3,4-methylenedioxymethamphetamine in the rat. Prog Neuropsychopharmacol Biol Psychiatry. 2000 Aug;24(6):955-77.
Ref 551380Differential behavioural and neurochemical effects of para-methoxyamphetamine and 3,4-methylenedioxymethamphetamine in the rat. Prog Neuropsychopharmacol Biol Psychiatry. 2000 Aug;24(6):955-77.

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