Scopolamine

Formula: C₁₇H₂₁NO₄
Molecular weight: 303.3529
IUPAC Standard InChI: InChI=1S/C17H21NO4/c1-18-13-7-11(8-14(18)16-15(13)22-16)21-17(20)12(9-19)10-5-3-2-4-6-10/h2-6,11-16,19H,7-9H2,1H3/t11-,12?,13?,14?,15-,16+
IUPAC Standard InChIKey: STECJAGHUSJQJN-MBBCWDQXSA-N
CAS Registry Number: 51-34-3
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript.
Stereoisomers:
- Aposcopolamine
- Methylscopolamine
Other names: Benzeneacetic acid, α-(hydroxymethyl)-, 9-methyl-3-oxa-9-azatricyclo[3.3.1.0(2,4)]non-7-yl ester, [7(S)-(1α,2β,4β,5α,7β)]-; 1αH,5αH-Tropan-3α-ol, 6β,7β-epoxy-, (-)-tropate (ester); (-)-Hyoscine; Atrochin; Atroquin; Hyosceine; Hyoscine; Scopine tropate; Skopolamin; SEE; 6,7-Epoxytropine tropate; 6-β,7-β-Epoxy-3-α-tropanyl S-(-)-tropate; Epoxytropine tropate; Hyosol; Oscine; 3-Oxa-9-azatricyclo(3.3.1.O(2,4))nonan-7-ol, 9-methyl-, tropate; Tropic acid, ester with scopine; Tropic acid, 9-methyl-3-oxa-9-azatricyclo(3.3.1.O(2,4))non-7-yl ester; 9-Methyl-3-oxa-9-azatricyclo[3.3.1.0(2,4)]nonan-7-ol (-)-tropate; l-Scopolamine; Transderm-Scop; 6β,7β-Epoxy-1αH,5αH-tropan-3α-ol (-)-tropate (ester); Scop; Scopoderm-TTS; Transcop; (-)-Scopolamine; Scopine (-)-tropate; 14797-94-5; 97991-84-9; 226562-00-1; 28901-63-5; 65319-33-7; 58670-87-4
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Information on this page:
Other data available:
- Mass spectrum (electron ionization)
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Gas Chromatography

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

Column type	Active phase	Temperature (C)	I	Reference	Comment
Packed	SE-30	240.	2315.	Musumarra, Scarlata, et al., 1987	N2, 1% se-30 on Anachrom ABS(80-100mesh); Column length: 2. m

Kovats' RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	HP-5MS	2263.	Doncheva, Berkov, et al., 2006	30. m/0.25 mm/0.25 μm, He, 4. K/min, 300. C @ 10. min; T_start: 50. C
Capillary	SE-30	2310.	Schepers, Wijsbeek, et al., 1982	25. m/0.49 mm/1.14 μm, 100. C @ 2. min, 8. K/min, 275. C @ 15. min

Kovats' RI, non-polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Packed	OV-101	2280.	McLinden and Stenhouse, 1979	N2, Chromosorb W; Column length: 2. m; Program: not specified

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	DB-1	2286.	Perrigo, Peel, et al., 1985	15. m/0.32 mm/0.25 μm, He, 8. K/min, 280. C @ 5. min; T_start: 120. C
Capillary	SE-30	2261.	Anderson and Stafford, 1983	15. m/0.25 mm/0.25 μm, He, 5. K/min; T_start: 100. C; T_end: 295. C
Packed	SE-30	2315.	Perrigo and Peel, 1981	N2, Chromosorb W, 130. C @ 2. min, 8. K/min, 290. C @ 8. min; Column length: 1.8 m

Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	HP-5MS	2395.4	Andriamaharavo, 2014	30. m/0.25 mm/0.25 μm, He; Program: 60C (1 min) => 5 C/min => 210C => 10 C/min => 280C (15 min)

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Packed	Polydimethyl siloxane	2303.	MHA, 9999	Nitrogen; Column length: 2. m; T_start: 100. C; T_end: 300. C
Packed	OV-1	2290.	Marozzi, Gambaro, et al., 1982	Gas Chrom P, 5. K/min; Column length: 2. m; T_start: 150. C; T_end: 300. C
Packed	SE-30	2320.	Marozzi, Gambaro, et al., 1982	Gas Chrom P, 5. K/min; Column length: 2. m; T_start: 150. C; T_end: 300. C

Normal alkane RI, non-polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	SE-54	2292.	Detzel and Wink, 1993	15. m/0.25 mm/0.16 μm, Helium; Program: 150 0C (2 min) 15 0C/min -> 250 0C 25 0C/min -> 200 0C (10 min)
Other	Methyl Silicone	2303.	Ardrey and Moffat, 1981	Program: not specified

References

Go To: Top, Gas Chromatography, Notes

Musumarra, Scarlata, et al., 1987
Musumarra, G.; Scarlata, G.; Romano, G.; Cappello, G.; Clementi, S.; Giulietti, G., Qualitative organic analysis. Part 2. Identification of drugs by principal components analysis of standardized TLC data in four eluent systems and of retention indices on SE 30, J. Anal. Toxicol., 1987, 11, 4, 154-163, https://doi.org/10.1093/jat/11.4.154 . [all data]

Doncheva, Berkov, et al., 2006
Doncheva, T.; Berkov, S.; Philipov, S., Comparative study of the alkaloids in tribe Datureae and their chemosystematic significance, Biochem. Syst. Ecol., 2006, 34, 6, 478-488, https://doi.org/10.1016/j.bse.2006.01.008 . [all data]

Schepers, Wijsbeek, et al., 1982
Schepers, P.; Wijsbeek, J.; Franke, J.P.; de Zeeuw, R.A., Applicability of capillary gas chromatography to substance identification in toxicology by means of retention indices, J. Forensic Sci., 1982, 27, 1, 49-60. [all data]

McLinden and Stenhouse, 1979
McLinden, V.J.; Stenhouse, A.M., A chromatography system for drug identification, Forensic Sci. Int., 1979, 13, 71-79, https://doi.org/10.1016/0379-0738(79)90265-2 . [all data]

Perrigo, Peel, et al., 1985
Perrigo, B.J.; Peel, H.W.; Ballantyne, D.J., Use of Dual-Column Fused-Silica Capillary Gas Chromatography in Combination with Detector Response Factors for Analytical Toxicology., J. Chromatogr., 1985, 341, 81-88, https://doi.org/10.1016/S0378-4347(00)84011-6 . [all data]

Anderson and Stafford, 1983
Anderson, W.H.; Stafford, D.T., Applications of capillary gas chromatography in routine toxicological analyses, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1983, 6, 5, 247-254, https://doi.org/10.1002/jhrc.1240060506 . [all data]

Perrigo and Peel, 1981
Perrigo, B.J.; Peel, H.W., The use of retention indices and temperature-programmed gas chromatography in analytical toxicology, J. Chromatogr. Sci., 1981, 19, 5, 219-226, https://doi.org/10.1093/chromsci/19.5.219 . [all data]

Andriamaharavo, 2014
Andriamaharavo, N.R., Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2014. [all data]

MHA, 9999
MHA, Directorate of ForensicScience., Forensic Toxicology, 9999. [all data]

Marozzi, Gambaro, et al., 1982
Marozzi, E.; Gambaro, V.; Saligari, E.; Mariani, R.; Lodi, F., Use of the retention index in gas chromatographic studies of drugs, J. Anal. Toxicol., 1982, 6, 4, 185-192, https://doi.org/10.1093/jat/6.4.185 . [all data]

Detzel and Wink, 1993
Detzel, A.; Wink, M., Attraction. deterrence or intoxication of bees (Apis mellifera) by plant allelochemicals, Chemoecology, 1993, 4, 1, 8-18, https://doi.org/10.1007/BF01245891 . [all data]

Ardrey and Moffat, 1981
Ardrey, R.E.; Moffat, A.C., Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase, J. Chromatogr., 1981, 220, 3, 195-252, https://doi.org/10.1016/S0021-9673(00)81925-1 . [all data]

Notes

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Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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