Compound: amantadine
SMILES: NC12CC3CC(C1)CC(C2)C3
InChIKey: DKNWSYNQZKUICI-UHFFFAOYSA-N
Synonyms: amantadine, 1-Adamantanamine, 768-94-5, adamantan-1-amine, 1-Adamantylamine, 1-Aminoadamantane, Adamantanamine, Adamantylamine, Amantidine, Aminoadamantane, Adamantamine, Pk-merz, Amantadina, Amantadinum, Gocovri, Viregyt, NSC-341865, Tricyclo[3.3.1.13,7]decan-1-amine, Tricyclo(3.3.1.1(sup 3.7))decan-1-amine, Virosol, BF4C9Z1J53, Tricyclo(3.3.1.13,7)decan-1-amine, DTXSID8022117, Tricyclo[3.3.1.1(3,7)]decan-1-amine, CHEBI:2618, DTXCID502117, 1 Aminoadamantane, Endantadine, tricyclo[3.3.1.1(3,7)]decan-1-ylamine, tricyclo[3.3.1.1(3,7)]decane-1-amine, tricyclo(3.3.1.1(3,7))decan-1-amine, tricyclo(3.3.1.1(3,7))decane-1-amine, tricyclo(3.3.1.1(3,7))decan-1-ylamine, GenAmantadine, InfectoFlu, Gen Amantadine, PMSAmantadine, Infecto Flu, AmantaSulfateAZU, PMS Amantadine, Amantadin AZU, AmantaHCIAZU, Stada, Amantadin, AL, Amantadin, Amantadinratiopharm, AZU, Amantadin, Amantadinneuraxpharm, Amantadin ratiopharm, Amanta HCI AZU, Sulfate, Amantadine, Amanta Sulfate AZU, Amantadin neuraxpharm, Juventus, Amantadina, Llorente, Amantadina, RefChem:5540, 212-201-2, 1-Adamantamine, Symadine, MFCD00074732, adamantan-1-ylamine, TCMDC-125869, 1-adamantaneamine, 1-Aminotricyclo(3.3.1.1(sup 3,7))decane, Amantadine (INN), NSC 341865, tricyclo[3.3.1.1~3,7~]decan-1-amine, CHEMBL660, adamantanylamine, NSC341865, (3s,5s,7s)-Tricyclo[3.3.1.1~3,7~]decan-1-Amine, NCGC00015036-03, Tricyclo[3.3.1.13,7]decane-1-amine, AMANTADINE [INN], Amantadine Base, Amantadine [INN:BAN], Amantadinum [INN-Latin], Amantadina [INN-Spanish], Amant, CAS-768-94-5, 40933-03-7, HSDB 3202, Tricyclo(3.3.1.1(3,7))-decan-1-amine, EINECS 212-201-2, ADAMANTANE,1-AMINO, adamantaneamine, BRN 2204333, UNII-BF4C9Z1J53, adamantyl amine, AmantadineHCl, 1-admantaneamine, 1-Amantadine, Tricyclo(3.3.1.1(sup 3,7))decan-1-amine, 1-adamantanylamine, 1-adamantyl amine, Adamant-1-ylamine, 1-amino-adamantane, adamantane-1-amine, 768-94-5 (FREE BASE), Mantadine (Salt/Mix), Symmetrel (Salt/Mix), Spectrum_000030, AMANTADINE [MI], Tricyclo[3.3.1.1^3,7]decan-1-amine, Prestwick0_000407, Prestwick1_000407, Prestwick2_000407, Prestwick3_000407, Spectrum2_000081, Spectrum3_000291, Spectrum4_000134, Spectrum5_000772, 1-Adamantylamine, 97%, AMANTADINE [HSDB], Lopac-A-1260, Tricyclo[3.3.1.1(sup3,7)]decan-1-amine, AMANTADINE [VANDF], EC 212-201-2, AMANTADINE [MART.], SCHEMBL4098, AMANTADINE [WHO-DD], NCIOpen2_001059, Lopac0_000004, Oprea1_248648, BSPBio_000334, BSPBio_001570, BSPBio_001822, KBioGR_000548, KBioSS_000390, BIDD:GT0757, DivK1c_000815, SCHEMBL480287, Exp-105-1 (Salt/Mix), SPBio_000002, SPBio_002273, BPBio1_000368, GTPL4128, orb1300103, orb3139273, SCHEMBL1525345, SCHEMBL3512411, SCHEMBL5999255, SCHEMBL8649324, SCHEMBL15672299, SCHEMBL18007744, SCHEMBL20409394, SCHEMBL21309814, SCHEMBL21310017, KBio1_000815, KBio2_000390, KBio2_002958, KBio2_005526, KBio3_001322, (3s,5s,7s)-adamantan-1-amine, NINDS_000815, HMS1791O12, HMS1989O12, HMS3604O07, HMS3887I19, HMS5087L14, ALBB-013871, HY-B0402, MSK10021, STR04703, Tox21_110068, BDBM50033369, EBC-26100, s5499, SBB071506, STK298781, AKOS000113994, AKOS000119324, AKOS007930692, AKOS015935124, Tox21_110068_1, CCG-204100, CS-W008656, DB00915, FA07678, SDCCGSBI-0049993.P005, IDI1_000815, NCGC00015036-01, NCGC00015036-02, NCGC00015036-04, NCGC00015036-05, NCGC00015036-06, NCGC00015036-07, NCGC00015036-08, NCGC00015036-09, NCGC00015036-11, NCGC00015036-13, NCGC00015036-24, NCGC00162039-01, NCGC00162039-02, NCGC00162039-03, NCGC00162039-04, NCGC00179597-01, AC-25879, AS-14215, BP-13040, ST097860, SY017655, 1-Adamantanamine (purified by sublimation), SBI-0049993.P004, WLN: L66 B6 A B- C 1B ITJ BZ, A2318, A3234, AB00514655, NS00007702, EN300-33893, tricyclo[3.3.1.1[3,7]]decane, 1-amino-, C06818, D07441, AB00053414-14, AB00053414-16, AB00053414_17, AB00053414_18, AB01275427-01, AE-641/01634060, F209082, L000868, Q409761, BRD-K70330367-003-01-2, BRD-K70330367-003-03-8, BRD-K70330367-003-07-9, BRD-K70330367-003-08-7, Q27453436, F0001-1962, InChI=1/C10H17N/c11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9H,1-6,11H
Theoretical properties:
molecular_formula: C10H17N
molecular_weight: 151.25 g/mol
exact_mass: 151.136099547 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 1
rotatable_bond_count: 0
heavy_atom_count: 11
topological_polar_surface_area: 26 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: HEXAKISTETRAHEDRAL CRYSTALS BY SUBLIMATION
color: HEXAKISTETRAHEDRAL CRYSTALS BY SUBLIMATION
melting_point: 180-192
Descriptions:
{"pubchem": "Amantadine is a member of the class of adamantanes that is used as an antiviral and antiparkinson drug. It has a role as an analgesic, a non-narcotic analgesic, an antiviral drug, an antiparkinson drug, a dopaminergic agent and a NMDA receptor antagonist. It is a primary aliphatic amine and a member of adamantanes. It is a conjugate base of an adamantan-1-aminium. It derives from a hydride of an adamantane.", "chebi": "A member of the class of  adamantanes that is used as an antiviral and  antiparkinson drug.", "chembl": "AMANTADINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Amantadine, sold under the brand name Gocovri among others, is a medication used to treat dyskinesia associated with parkinsonism and influenza caused by type A influenzavirus, though its use for the latter is no longer recommended because of widespread drug resistance. It is also used for a variety of other conditions. The drug is taken by mouth.\nAmantadine has a mild side-effect profile. Common neurological side effects include drowsiness, lightheadedness, dizziness, and confusion. Because of its effects on the central nervous system (CNS), it should be combined cautiously with additional CNS stimulants or anticholinergic drugs. Given that it is  cleared by the kidneys, amantadine is contraindicated in persons with end-stage kidney disease. Due to its anticholinergic effects, it should be taken with caution by those with enlarged prostates or glaucoma.\nThe pharmacology of amantadine is complex. It acts as a sigma \u03c31 receptor agonist, nicotinic acetylcholine receptor negative allosteric modulator, dopaminergic agent, and weak NMDA receptor antagonist, among other actions. The precise mechanism of action of its therapeutic effects in the treatment of CNS disorders is unclear. The antiviral mechanism of action is inhibition of the influenza virus A M2 proton channel, which prevents endosomal escape (i.e., the release of viral genetic material into the host cytoplasm). Amantadine is an adamantane derivative and is related to memantine and rimantadine.\nAmantadine was first used for the treatment of influenza A. After its antiviral properties were initially reported in 1963, amantadine received approval for prophylaxis against the influenza virus A in 1966. In 1968, its antiparkinsonian effects were serendipitously discovered. In 1973, the Food and Drug Administration (FDA) approved amantadine for use in the treatment of Parkinson's disease. In 2020, the extended-release formulation was approved for use in the treatment of levodopa-induced dyskinesia."}