Compound: doxylamine
SMILES: O(C(c1ncccc1)(c2ccccc2)C)CCN(C)C
InChIKey: HCFDWZZGGLSKEP-UHFFFAOYSA-N
Synonyms: doxylamine, 469-21-6, Dossilamina, Doxylaminum, Doxilminio, doxilamina, 2-Dimethylaminoethoxyphenylmethyl-2-picoline, N,N-Dimethyl-2-(1-phenyl-1-(2-pyridinyl)ethoxy)ethanamine, Phenyl-2-pyridylmethyl-beta-N,N-dimethylaminoethyl ether, dimethyl({2-[1-phenyl-1-(pyridin-2-yl)ethoxy]ethyl})amine, 2-(alpha-(2-(Dimethylamino)ethoxy)-alpha-methylbenzyl)pyridine, 95QB77JKPL, Ethanamine, N,N-dimethyl-2-(1-phenyl-1-(2-pyridinyl)ethoxy)-, DTXSID1022970, CHEBI:51380, Pyridine, 2-(alpha-(2-(dimethylamino)ethoxy)-alpha-methylbenzyl)-, Ethanamine, N,N-dimethyl-2-[1-phenyl-1-(2-pyridinyl)ethoxy]-, dimethyl((2-(1-phenyl-1-(pyridin-2-yl)ethoxy)ethyl))amine, (+-)-Doxylamine, RefChem:55070, DTXCID102970, R06AA09, 207-414-2, (+/-)-Doxylamine, N,N-dimethyl-2-(1-phenyl-1-pyridin-2-ylethoxy)ethanamine, NCI C60684, Doxylamine (INN), Doxylaminephenyl-d5, S-Doxylamine, Dossilamina [DCIT], Alsadorm, Doxylaminum [INN-Latin], Doxilminio [INN-Spanish], Decapryn (TN), DOXYLAMINE [INN], Doxylamine [INN:BAN], Pyridine, 2-[.alpha.-[2-(dimethylamino)ethoxy]-.alpha.-methylbenzyl]-, HSDB 5184, EINECS 207-414-2, UNII-95QB77JKPL, BRN 0230379, ()-Doxylamine, PYRIDINE, 2-(.ALPHA.-(2-(DIMETHYLAMINO)ETHOXY)-.ALPHA.-METHYLBENZYL)-, N,N-Dimethyl-2-[(1S)-1-phenyl-1-(2-pyridinyl)ethoxy]ethanamine; (S)-N,N-Dimethyl-2-(1-phenyl-1-(pyridin-2-yl)ethoxy)ethanamine, Spectrum_001014, N,N-dimethyl-2-[1-phenyl-1-(pyridin-2-yl)ethoxy]ethanamine, DOXYLAMINE [MI], Prestwick0_000027, Prestwick1_000027, Prestwick2_000027, Prestwick3_000027, Spectrum2_000115, Spectrum3_000409, Spectrum4_000528, Spectrum5_000949, DOXYLAMINE [HSDB], DOXYLAMINE [VANDF], EC 207-414-2, SCHEMBL4709, CHEMBL1004, DOXYLAMINE [WHO-DD], Lopac0_000348, BSPBio_000093, BSPBio_001938, KBioGR_001135, KBioSS_001494, 5-21-03-00508 (Beilstein Handbook Reference), DivK1c_000841, SPBio_000130, SPBio_002014, BPBio1_000103, GTPL7171, SCHEMBL30702275, KBio1_000841, KBio2_001494, KBio2_004062, KBio2_006630, KBio3_001158, MSK2841, NINDS_000841, HMS3604L05, N,N-dimethyl-2-[(1-phenyl-1-pyridin-2-ylethyl)oxy]ethanamine, RFC84933, EBC-06825, MFCD00599469, STL018676, AKOS005657227, CCG-204443, DB00366, SDCCGSBI-0050336.P005, IDI1_000841, ( inverted exclamation markA)-Doxylamine, NCGC00021147-02, NCGC00021147-03, NCGC00021147-04, NCGC00021147-05, NCGC00021147-06, NCGC00021147-08, NCGC00021147-09, NCGC00021147-13, NCGC00021147-21, NCGC00089789-02, NCGC00089789-04, NCGC00089789-05, AC-15949, SBI-0050336.P004, DB-051407, AB00053466, NS00000474, D07878, EN300-123421, AB00053466-18, AB00053466_19, AB00053466_20, .alpha.-Dimethylaminoethoxyphenylmethyl-2-picoline, L001076, Q423390, BRD-A44008656-036-05-0, BRD-A44008656-036-15-9, BRD-A44008656-036-24-1, BRD-A44008656-036-25-8, Z2242151271, N,N-dimethyl-2-[1-phenyl-1-(2-pyridyl)ethoxy]ethanamine, Phenyl-2-pyridylmethyl-.beta.-N,N-dimethylaminoethyl ether, N,N-Dimethyl-2-[1-phenyl-1-(2-pyridinyl)ethoxy]ethanamine #, 2-(.alpha.-(2-(Dimethylamino)ethoxy)-.alpha.-methylbenzyl)pyridine, N,N-Dimethyl-2-[1-phenyl-1-(pyridin-2-yl)ethoxy]ethan-1-amine, 2-(.ALPHA.(2-(DIMETHYLAMINO)ETHOXY)-.ALPHA.-METHYLBENZYL)PYRIDINE
Theoretical properties:
molecular_formula: C17H22N2O
molecular_weight: 270.37 g/mol
exact_mass: 270.173213330 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 6
heavy_atom_count: 20
topological_polar_surface_area: 25.4 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: LIQ
color: LIQ
boiling_point: 279 to 286 °F at 0.5 mmHg (NTP, 1992)
melting_point: < 25 °C
vapor_pressure: Slightly volatile
Descriptions:
pubchem: Doxylamine is a member of pyridines and a tertiary amine. It has a role as a sedative, a H1-receptor antagonist, a histamine antagonist, a cholinergic antagonist, an anti-allergic agent, an antiemetic and an antitussive.
chembl: DOXYLAMINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Doxylamine is an antihistamine medication used to treat insomnia and allergies, and—in combination with pyridoxine (vitamin B6)—to treat morning sickness in pregnant women. It is available over-the-counter and is sold under such brand names as Equate and Unisom, among others; and it is used in nighttime cold medicines (e.g., NyQuil) and pain medications containing paracetamol (acetaminophen) or codeine to help with sleep. The medication is delivered chemically by the salt doxylamine succinate and is taken by mouth. Doxylamine and other first-generation antihistamines are the most widely used sleep medications in the world. Typical side effects of doxylamine include dizziness, drowsiness, grogginess, and dry mouth, among others. 
As an antihistamine, doxylamine is an inverse agonist of the histamine H1 receptor. As a first-generation antihistamine, it typically crosses the blood–brain barrier into the brain, thereby producing a suite of sedative and hypnotic effects that are mediated by the central nervous system.  
Doxylamine is also a potent anticholinergic, meaning that it causes delirium at high doses (i.e., at much higher doses than recommended). Specifically, it is an antagonist of the muscarinic acetylcholine receptors M1 through M5. These sedative and deliriant effects have in some cases led to the drug being used recreationally. Doxylamine was first described in 1948 or 1949.