Input interpretation
sertraline
Chemical names and formulas
formula | C_17H_17Cl_2N name | sertraline IUPAC name | (1S, 4S)-4-(3, 4-dichlorophenyl)-N-methyl-1, 2, 3, 4-tetrahydronaphthalen-1-amine mass fractions | C (carbon) 66.7% | Cl (chlorine) 23.2% | H (hydrogen) 5.6% | N (nitrogen) 4.57%
Lewis structure
Draw the Lewis structure of sertraline. Start by drawing the overall structure of the molecule, ignoring potential double and triple bonds: Count the total valence electrons of the carbon (n_C, val = 4), chlorine (n_Cl, val = 7), hydrogen (n_H, val = 1), and nitrogen (n_N, val = 5) atoms: 17 n_C, val + 2 n_Cl, val + 17 n_H, val + n_N, val = 104 Calculate the number of electrons needed to completely fill the valence shells for carbon (n_C, full = 8), chlorine (n_Cl, full = 8), hydrogen (n_H, full = 2), and nitrogen (n_N, full = 8): 17 n_C, full + 2 n_Cl, full + 17 n_H, full + n_N, full = 194 Subtracting these two numbers shows that 194 - 104 = 90 bonding electrons are needed. Each bond has two electrons, so in addition to the 39 bonds already present in the diagram add 6 bonds. To minimize formal charge carbon wants 4 bonds. Identify the atoms that want additional bonds and the number of electrons remaining on each atom: Fill in the 6 bonds by pairing electrons between adjacent highlighted atoms. Note that the six atom rings are aromatic, so that the single and double bonds may be rearranged: Answer: | |
3D structure
3D structure
Basic properties
molar mass | 306.2 g/mol phase | solid (at STP)
Units
Hydrophobicity and permeability properties
experimental LogP hydrophobicity | 5.1 predicted LogP hydrophobicity | 5.06 predicted LogS | -6.32
Basic drug properties
approval status | approved | small molecule drug categories | antidepressant | antidepressive agent | selective serotonin reuptake inhibitor (SSRI) | serotonin uptake inhibitor dosage forms | oral: capsule
brand names | apo-sertraline | lustral | zoloft
Chemical identifiers
CAS number | 79617-96-2 PubChem CID number | 68617 PubChem SID number | 210738 SMILES identifier | CNC1CCC(C2=CC=CC=C12)C3=CC(=C(C=C3)Cl)Cl InChI identifier | InChI=1/C17H17Cl2N/c1-20-17-9-7-12(13-4-2-3-5-14(13)17)11-6-8-15(18)16(19)10-11/h2-6, 8, 10, 12, 17, 20H, 7, 9H2, 1H3/t12-, 17-/m0/s1 InChI key | VGKDLMBJGBXTGI-SJCJKPOMBV