Record Information |
---|
Version | 5.0 |
---|
Status | Expected but not Quantified |
---|
Creation Date | 2012-09-06 15:16:49 UTC |
---|
Update Date | 2022-03-07 02:51:38 UTC |
---|
HMDB ID | HMDB0014502 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | Mefloquine |
---|
Description | Mefloquine is only found in individuals that have used or taken this drug. It is a phospholipid-interacting antimalarial drug (antimalarials). It is very effective against plasmodium falciparum with very few side effects. [PubChem]Mefloquine has been found to produce swelling of the Plasmodium falciparum food vacuoles. It may act by forming toxic complexes with free heme that damage membranes and interact with other plasmodial components. |
---|
Structure | OC(C1CCCCN1)C1=CC(=NC2=C1C=CC=C2C(F)(F)F)C(F)(F)F InChI=1S/C17H16F6N2O/c18-16(19,20)11-5-3-4-9-10(15(26)12-6-1-2-7-24-12)8-13(17(21,22)23)25-14(9)11/h3-5,8,12,15,24,26H,1-2,6-7H2 |
---|
Synonyms | Value | Source |
---|
alpha-2-Piperidinyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol | ChEBI | a-2-Piperidinyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol | Generator | Α-2-piperidinyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol | Generator | Mefloquinone | HMDB | Hoffmann la roche brand OF mefloquine hydrochloride | HMDB | Hoffmann-la roche brand OF mefloquine hydrochloride | HMDB | Mefloquine hydrochloride | HMDB | Roche brand OF mefloquine hydrochloride | HMDB | Lariam | HMDB | Mephloquine | HMDB | Mefloquine | HMDB |
|
---|
Chemical Formula | C17H16F6N2O |
---|
Average Molecular Weight | 378.3122 |
---|
Monoisotopic Molecular Weight | 378.116682374 |
---|
IUPAC Name | [2,8-bis(trifluoromethyl)quinolin-4-yl](piperidin-2-yl)methanol |
---|
Traditional Name | mefloquine |
---|
CAS Registry Number | 53230-10-7 |
---|
SMILES | OC(C1CCCCN1)C1=CC(=NC2=C1C=CC=C2C(F)(F)F)C(F)(F)F |
---|
InChI Identifier | InChI=1S/C17H16F6N2O/c18-16(19,20)11-5-3-4-9-10(15(26)12-6-1-2-7-24-12)8-13(17(21,22)23)25-14(9)11/h3-5,8,12,15,24,26H,1-2,6-7H2 |
---|
InChI Key | XEEQGYMUWCZPDN-UHFFFAOYSA-N |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as 4-quinolinemethanols. These are organoheterocyclic compounds containing a quinoline moiety substituted at the 4-position with a methanol. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organoheterocyclic compounds |
---|
Class | Quinolines and derivatives |
---|
Sub Class | 4-quinolinemethanols |
---|
Direct Parent | 4-quinolinemethanols |
---|
Alternative Parents | |
---|
Substituents | - 4-quinolinemethanol
- Aralkylamine
- Piperidine
- Pyridine
- Benzenoid
- Heteroaromatic compound
- 1,2-aminoalcohol
- Secondary alcohol
- Secondary aliphatic amine
- Secondary amine
- Azacycle
- Hydrocarbon derivative
- Organopnictogen compound
- Organic oxygen compound
- Organooxygen compound
- Organonitrogen compound
- Organofluoride
- Organohalogen compound
- Organic nitrogen compound
- Amine
- Alkyl halide
- Alcohol
- Aromatic alcohol
- Alkyl fluoride
- Aromatic heteropolycyclic compound
|
---|
Molecular Framework | Aromatic heteropolycyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
Physiological effect | Not Available |
---|
Disposition | |
---|
Process | Not Available |
---|
Role | Not Available |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Molecular Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.038 g/L | Not Available | LogP | 3.9 | Not Available |
|
---|
Experimental Chromatographic Properties | Not Available |
---|
Predicted Molecular Properties | |
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
---|
Mefloquine,1TMS,isomer #1 | C[Si](C)(C)OC(C1=CC(C(F)(F)F)=NC2=C(C(F)(F)F)C=CC=C12)C1CCCCN1 | 1991.5 | Semi standard non polar | 33892256 | Mefloquine,1TMS,isomer #2 | C[Si](C)(C)N1CCCCC1C(O)C1=CC(C(F)(F)F)=NC2=C(C(F)(F)F)C=CC=C12 | 2089.5 | Semi standard non polar | 33892256 | Mefloquine,2TMS,isomer #1 | C[Si](C)(C)OC(C1=CC(C(F)(F)F)=NC2=C(C(F)(F)F)C=CC=C12)C1CCCCN1[Si](C)(C)C | 2122.9 | Semi standard non polar | 33892256 | Mefloquine,2TMS,isomer #1 | C[Si](C)(C)OC(C1=CC(C(F)(F)F)=NC2=C(C(F)(F)F)C=CC=C12)C1CCCCN1[Si](C)(C)C | 2276.7 | Standard non polar | 33892256 | Mefloquine,2TMS,isomer #1 | C[Si](C)(C)OC(C1=CC(C(F)(F)F)=NC2=C(C(F)(F)F)C=CC=C12)C1CCCCN1[Si](C)(C)C | 2328.7 | Standard polar | 33892256 | Mefloquine,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(C1=CC(C(F)(F)F)=NC2=C(C(F)(F)F)C=CC=C12)C1CCCCN1 | 2187.2 | Semi standard non polar | 33892256 | Mefloquine,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N1CCCCC1C(O)C1=CC(C(F)(F)F)=NC2=C(C(F)(F)F)C=CC=C12 | 2304.2 | Semi standard non polar | 33892256 | Mefloquine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(C1=CC(C(F)(F)F)=NC2=C(C(F)(F)F)C=CC=C12)C1CCCCN1[Si](C)(C)C(C)(C)C | 2523.7 | Semi standard non polar | 33892256 | Mefloquine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(C1=CC(C(F)(F)F)=NC2=C(C(F)(F)F)C=CC=C12)C1CCCCN1[Si](C)(C)C(C)(C)C | 2676.0 | Standard non polar | 33892256 | Mefloquine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(C1=CC(C(F)(F)F)=NC2=C(C(F)(F)F)C=CC=C12)C1CCCCN1[Si](C)(C)C(C)(C)C | 2521.1 | Standard polar | 33892256 |
|
---|
| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - Mefloquine GC-MS (Non-derivatized) - 70eV, Positive | splash10-001i-9025000000-bd2efec95144343a1b49 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Mefloquine GC-MS (1 TMS) - 70eV, Positive | splash10-0006-9880700000-0d7f5ede34418b735bf8 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Mefloquine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Mefloquine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Mefloquine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Mefloquine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mefloquine 10V, Positive-QTOF | splash10-03fr-0009000000-f63c2940b613df55b83d | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mefloquine 20V, Positive-QTOF | splash10-03di-4029000000-054581384c6b5a51066d | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mefloquine 40V, Positive-QTOF | splash10-001i-9041000000-1e6b869ab2fa3ffa6785 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mefloquine 10V, Negative-QTOF | splash10-004i-0009000000-f43f6cd574501c04be1d | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mefloquine 20V, Negative-QTOF | splash10-0a6r-2019000000-deffba940fff3f2a8a5c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mefloquine 40V, Negative-QTOF | splash10-001i-9042000000-cda7cad59a1c31fcc399 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mefloquine 10V, Positive-QTOF | splash10-004i-0009000000-0c5583423999f9b76541 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mefloquine 20V, Positive-QTOF | splash10-01t9-1009000000-c8c4028b3773cf47d2c3 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mefloquine 40V, Positive-QTOF | splash10-0536-9067000000-f1c1030c0e913181f813 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mefloquine 10V, Negative-QTOF | splash10-004i-0009000000-826539601dd4ffcd5acc | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mefloquine 20V, Negative-QTOF | splash10-004i-0029000000-cab8b26d4d2c51fe26ef | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mefloquine 40V, Negative-QTOF | splash10-004i-1059000000-9cd7452365f680e2e6a5 | 2021-09-22 | Wishart Lab | View Spectrum |
|
---|