morphinanymous
Bluelighter
I found this in
What I guess are the Micro Gram articles. I hadn't looked at them in a while and this influx of designer drug/ rc's where I live sparked my curiosity so I decided to see what they thought about it. I find it funny that the top reference for the entire article is a VICE magazine article. I love Vice and have always thought it to be funny, filthy, and informing. In a way I look at this as a good thing, the DEA cannot find enough information on their own or probably to lazy to try and discover/use science to figure their own problems out.
This is the title of the report:
The Characterization of 2-(3-Methoxyphenyl)-2-(ethylamino)cyclohexanone
(Methoxetamine)
Patrick A. Hays*, John F. Casale, and Arthur L. Berrier
U.S. Department of Justice
Drug Enforcement Administration
Special Testing and Research Laboratory
22624 Dulles Summit Court
Dulles, VA 20166-9509
[email address withheld at authors’ request]
This is the last page were after a paragraph the references are listed:
When
methoxetamine HCl is compared to ketamine HCl, significant
differences can differentiate the compounds, especially the
absorbances at 1550-1600 cm-1 due to C-C stretching [5].
Synthesis
Methoxetamine was synthesized utilizing an analogous
procedure for that of ketamine (Figure 3). A cyclopentyl
Grignard was reacted with 3-methoxybenzonitrile to form
3-methoxyphenyl cyclopentyl ketone, which was then
brominated alpha to the ketone. The alpha-bromo ketone was
converted to the Schiff’s base with ethyl amine, which was then
heated to form methoxetamine. The NMR, FTIR, and mass
spectrum of the synthesized methoxetamine were in all respects
identical to the unknown compound’s spectra. Mass spectra for
the three intermediates are illustrated in Figure 11. GC
retention time data for the respective compounds are presented
in Table 1.
A significant amount of a by-product (impurity) was
produced during the synthesis of methoxetamine. The FTIR
(Figure 12a) of the synthesis impurity indicated that a carbonyl
was present and its mass spectrum (Figure 12b) indicated a
molecular weight of 247. The impurity was easily isolated
from methoxetamine HCl by its solubility in acetone. The
NMR spectrum (Figures 13 and 14) illustrated that this
compound, like methoxetamine, contained a 1,3-disubstituted
benzene (with a methoxy group at C3), an N-ethyl group, a
ketone, a quaternary carbon, and an n-butyl chain. However,
the proton and carbon chemical shifts and the HMBC
correlations show that the ketone is the bridge between the
benzene ring and a cyclopentyl ring and this cyclopentyl
ring contains the quaternary carbon which is bonded to the
N-ethyl group. The isolated impurity was characterized as
[1-(ethylamino)cyclopentyl](3-methoxyphenyl)methanone
(Figure 15).
References
1. Interview with a ketamine chemist or to be more precise,
an arylcyclohexylamine chemist. http://www.vice.com/
read/interview-with-ketamine-chemist-704-v18n2. Last
accessed December 1, 2011.2. Code of Federal Regulations. 21 U.S.C. § 802(32)(A).
3. Stevens CL. Aminoketones and methods for their
production, US Patent 3,254,124. May 31, 1966.
4. Smith RM. Understanding mass spectra. 2nd ed. John
Wiley and Sons, New York, NY 2004:340.
5. Silverstein RM, Bassler GC, Morrill TC. Spectrometric
identification of organic compounds. 4th ed. John Wiley
and Sons, New York, NY 1981:123.
Table 1 - Gas chromatographic retention times (Rt) for the methoxetamine and related compoundsa.
Compound Rt (min)
3-methoxyphenyl cyclopentyl ketone 14.50
1-hydroxycyclopentyl-(3-methoxyphenyl)-ketone-N-ethylimine 16.31
ketamine 16.51
methoxetamine 17.21
[1-(ethylamino)cyclopentyl](3-methoxyphenyl)methanone 17.35
alpha-bromo-(3-methoxyphenyl)-cyclopentyl ketone 17.54
aConditions given in the experimental section.
Figure 15 - Structure of methoxetamine impurity
Website below:
http://www.justice.gov/dea/programs/forensicsci/microgram/journal2012/mj9-1_3-17.pdf
What I guess are the Micro Gram articles. I hadn't looked at them in a while and this influx of designer drug/ rc's where I live sparked my curiosity so I decided to see what they thought about it. I find it funny that the top reference for the entire article is a VICE magazine article. I love Vice and have always thought it to be funny, filthy, and informing. In a way I look at this as a good thing, the DEA cannot find enough information on their own or probably to lazy to try and discover/use science to figure their own problems out.
This is the title of the report:
The Characterization of 2-(3-Methoxyphenyl)-2-(ethylamino)cyclohexanone
(Methoxetamine)
Patrick A. Hays*, John F. Casale, and Arthur L. Berrier
U.S. Department of Justice
Drug Enforcement Administration
Special Testing and Research Laboratory
22624 Dulles Summit Court
Dulles, VA 20166-9509
[email address withheld at authors’ request]
This is the last page were after a paragraph the references are listed:
When
methoxetamine HCl is compared to ketamine HCl, significant
differences can differentiate the compounds, especially the
absorbances at 1550-1600 cm-1 due to C-C stretching [5].
Synthesis
Methoxetamine was synthesized utilizing an analogous
procedure for that of ketamine (Figure 3). A cyclopentyl
Grignard was reacted with 3-methoxybenzonitrile to form
3-methoxyphenyl cyclopentyl ketone, which was then
brominated alpha to the ketone. The alpha-bromo ketone was
converted to the Schiff’s base with ethyl amine, which was then
heated to form methoxetamine. The NMR, FTIR, and mass
spectrum of the synthesized methoxetamine were in all respects
identical to the unknown compound’s spectra. Mass spectra for
the three intermediates are illustrated in Figure 11. GC
retention time data for the respective compounds are presented
in Table 1.
A significant amount of a by-product (impurity) was
produced during the synthesis of methoxetamine. The FTIR
(Figure 12a) of the synthesis impurity indicated that a carbonyl
was present and its mass spectrum (Figure 12b) indicated a
molecular weight of 247. The impurity was easily isolated
from methoxetamine HCl by its solubility in acetone. The
NMR spectrum (Figures 13 and 14) illustrated that this
compound, like methoxetamine, contained a 1,3-disubstituted
benzene (with a methoxy group at C3), an N-ethyl group, a
ketone, a quaternary carbon, and an n-butyl chain. However,
the proton and carbon chemical shifts and the HMBC
correlations show that the ketone is the bridge between the
benzene ring and a cyclopentyl ring and this cyclopentyl
ring contains the quaternary carbon which is bonded to the
N-ethyl group. The isolated impurity was characterized as
[1-(ethylamino)cyclopentyl](3-methoxyphenyl)methanone
(Figure 15).
References
1. Interview with a ketamine chemist or to be more precise,
an arylcyclohexylamine chemist. http://www.vice.com/
read/interview-with-ketamine-chemist-704-v18n2. Last
accessed December 1, 2011.2. Code of Federal Regulations. 21 U.S.C. § 802(32)(A).
3. Stevens CL. Aminoketones and methods for their
production, US Patent 3,254,124. May 31, 1966.
4. Smith RM. Understanding mass spectra. 2nd ed. John
Wiley and Sons, New York, NY 2004:340.
5. Silverstein RM, Bassler GC, Morrill TC. Spectrometric
identification of organic compounds. 4th ed. John Wiley
and Sons, New York, NY 1981:123.
Table 1 - Gas chromatographic retention times (Rt) for the methoxetamine and related compoundsa.
Compound Rt (min)
3-methoxyphenyl cyclopentyl ketone 14.50
1-hydroxycyclopentyl-(3-methoxyphenyl)-ketone-N-ethylimine 16.31
ketamine 16.51
methoxetamine 17.21
[1-(ethylamino)cyclopentyl](3-methoxyphenyl)methanone 17.35
alpha-bromo-(3-methoxyphenyl)-cyclopentyl ketone 17.54
aConditions given in the experimental section.
Figure 15 - Structure of methoxetamine impurity
Website below:
http://www.justice.gov/dea/programs/forensicsci/microgram/journal2012/mj9-1_3-17.pdf
.