Synthesis of deuterium labeled tryptamine derivatives

Article abstract of DOI:10.1002/jccs.200700194

The synthesis of deuterium labeled tryptamine derivatives, [2-(1H-indol-3-yl)-[²H₄]-ethyl]-dimethylamine (DMT), [²H₁₀]-diethyl-[2-(1H-indol-3-yl)-ethyl]-amine (DET), [2-(1H-indol-3-yl)-ethyl]-[²H₆]-dipropyl-amine (DPT) and [²H₂]-alpha-methyltryptamine (AMT) is described. The isotopically labeled compounds are used as internal standards in gas chromatography-mass spectrometry (GC-MS) assays.

Full text of DOI:10.1002/jccs.200700194

Journal of the Chinese Chemical Society, 2007, 54, 1363-1368
1363
Synthesis of Deuterium Labeled Tryptamine Derivatives
Yu-Yun Wang (
Department of Chemistry, National Dong Hwa University, Soufeng, Hualien 974, Taiwan, R.O.C.
) and Chinpiao Chen* (
)
2
The synthesis of deuterium labeled tryptamine derivatives, [2-(1H-indol-3-yl)-[ H
4
]-ethyl]-dimethyl-
2
2
amine (DMT), [ H10]-diethyl-[2-(1H-indol-3-yl)-ethyl]-amine (DET), [2-(1H-indol-3-yl)-ethyl]-[ H
6
]-
2
dipropyl-amine (DPT) and [ H
2
]-alpha-methyltryptamine (AMT) is described. The isotopically labeled
compounds are used as internal standards in gas chromatography-mass spectrometry (GC-MS) assays.
Keywords: DMT; DET; DPT; AMT; Deuterium labeled; Internal standard.
INTRODUCTION
of deuterium-labeled control drugs as internal standards for
1
4–24
GC-MS analysis.
2
This work describes synthetic routes
2
2
2
Alpha-methyltryptamine (AMT), which is an indole
4 6 2
to [ H ]-DMT, [ H10]-DET, [ H ]-DPT and [ H ]-AMT and
analogue of amphetamine, was investigated in the 1960s as
an antidepressant, stimulant, and monoamine oxidase in-
hibitor. Today, AMT is recognized as a powerful psyche-
delic drug used by high school and college-aged men and
presents related characteristic analytical data. No report
has addressed these compounds.
1
-2
women. N,N-Dimethyltryptamine (DMT) is a hallucino-
genic indole alkaloid that occurs naturally in a variety of
plants and preparations used by ancient and modern South
American cultures when performing shamanistic divina-
RESULTS AND DISCUSSION
2
5-30
32
Although tryptamine derivatives DMT,
33-35
DET,
3
DPT and AMT
2
have been readily prepared via sev-
3
tion rituals. Notably, DMT occurs naturally in the mam-
-6
2
2
eral synthetic routes, preparation of [ H
4
]-DMT, [ H10]-
]-AMT has not been described.
Scheme I presents the general synthetic scheme for pre-
7
-12
2
2
malian brain as a neurotransmitter.
Diethyl-tryptamine
6 2
DET, [ H ]-DPT and [ H
(
DET) is an orally active hallucinogenic drug and psyche-
2
paring [ H
2
]-DMT (8), [ H10]-DET (5), [ H
2
delic compound with effects that last for a moderate dura-
tion. The DET is a substituted for diethyl groups and struc-
4
6
]-DPT (6) and
2
[ H
2
]-AMT (11). Compound 4 was prepared by reacting
1
3
turally similar to DMT and dipropyltryptamine (DPT).
indole 1 and oxalyl chloride to yield (1H-indol-3-yl)-oxo-
acetyl chloride (2); compound 2 was then treated with am-
monium hydroxide to form 2-(1H-indol-3-yl)-2-oxo-acet-
amide (3) in an 89% yield. Reduction of compound 3 with
lithium aluminum hydride produced 2-(1H-indol-3-yl)-
Dipropyltryptamine, a psychedelic drug belonging to the
tryptamine family, is found either as a crystalline hydro-
chloride salt or as an oily or crystalline base. When smoked,
the effects of DPT onset is in minutes and lasts for less than
one hour.
ethylamine (4) in a 70% yield. Compound 5 was prepared
2
by reacting compound 4 and [ H
Unknown drugs that are abused are typically detected
and identified by gas chromatography-mass spectrometry
5
]-iodoethane in the pres-
ence of potassium carbonate in a 20% yield. Compound 6
(
GC-MS) due to the high sensitivity of GC-MS and its abil-
was synthesized using the same conditions as that for pre-
2
paring compound 5 in the presence of [ H
ity to separate complex mixtures of organic compounds.
The abuse of psychoactive tryptamine derivatives has be-
come a very serious social problem. Standard samples for
analyzing controlled drugs in Taiwan are very difficult to
obtain. Many researchers are interested in the preparation
3
]-iodopropane
2
(ICH
2 2 3
CH C[ H ]) in a 68% yield. Synthesis of compound 8
followed the same conditions as those for preparing com-
2
pound 5 in the presence of [ H
3
]-iodomethane; however,
compound 8 was not obtained. Instead of compound 8, qua-
*
Corresponding author. Tel: +886-3-8633597; Fax: +886-3-8630475; E-mail: chinpiao@mail.ndhu.edu.tw

1
364 J. Chin. Chem. Soc., Vol. 54, No. 5, 2007
Wang and Chen
Scheme I
ternary ammonium salt was obtained. Quaternary ammo-
nium salt was applied to convert to compound 8 via treat-
ment with n-butyllithium or superhydride, but we did not
obtain the desired product 8. Alternatively, the following
pathway successfully yielded compound 8. A reaction of
compound 2 and dimethylamine formed 2-(1H-indol-3-
analysis. Therefore, deuterium-labeled compounds possess
the potential for use as an internal standard in GC-MS anal-
ysis.
EXPERIMENTAL SECTION
General Chemical Procedures
yl)-N,N-dimethyl-2-oxo-acetamide (7) in a 92% yield. The
2
reduction of compound 7 with lithium aluminum [ H
4
]-hy-
2
dride produced [2-(1H-indol-3-yl)-[ H
1
4
]-ethyl]-dimethyl-
H NMR spectra were obtained at 300 or 400 MHz
1
3
amine (8) in an 85% yield. A reaction of indole-3-carbox-
aldehyde (9) and nitroethane formed 3-(2-nitro-propenyl)-
(indicated in each case), and C NMR spectra were ob-
tained at 75.5 or 100.6 MHz using a Bruker NMR spec-
trometer. Chemical shifts (d) are reported in ppm relative to
1
H-indole (10) in a 63% yield. The reduction of compound
2
1
0 with lithium aluminum [ H
4
]-hydride produced 2-(1H-
]-ethylamine (11) in a 95% yield.
In conclusion, this study demonstrates the syntheses
of DMT-d , DET-d10, DPT-d and AMT-d . Although the
3
CHCl (7.26 and 77.0 ppm). Mass spectra (MS) were ob-
2
indol-3-yl)-1-methyl-[ H
2
tained using a Micromass Platform II mass spectrometer at
70 eV. High-resolution mass spectra (HRMS) were ob-
tained using a Finnigan/Thermo Quest MAT 95XL mass
spectrometer. Infrared spectra were recorded using an ATI
Mattson spectrometer. All reactions were performed in an-
hydrous solvents. Tetrahydrofuran and diethyl ether were
distilled from sodium-benzophenone in argon. Benzene
4
6
2
retention times of gas chromatography (GC) of labeled and
unlabeled compounds vary very little, quantification by
mass spectrometry (MS) with the selected ion monitoring
(
SIM) technique enhances the performance of quantitative

Synthesis of Deuterium Labeled Tryptamine Derivatives
J. Chin. Chem. Soc., Vol. 54, No. 5, 2007 1365
and N,N-dimethylformamide were distilled from calcium
hydride. All air-sensitive reactions were performed in dry
glassware under nitrogen using a standard glovebox. Flash
column chromatography was performed using MN silica
gel 60 (70-230 mesh) which was purchased from Macherey-
Nagel. Deuterium labeled compounds were purchased
from Cambridge Isotope Laboratories, Inc.
3
(300 MHz, CDCl , d): 8.02 (s, br, 1H), 7.63 (d, J = 7.9 Hz,
1H), 7.37 (d, J = 8.1 Hz, 1H), 7.21 (t, J = 7.5 Hz, 1H), 7.12
(t, J = 7.4 Hz, 1H), 7.05 (s, 1H), 3.04 (t, J = 6.5 Hz, 2H),
2.92 (t, J = 6.5 Hz, 2H). IR (KBr, thin film): 3343, 3280,
3029, 2868, 1591, 1453, 1345, 1232, 1109, 1007, 934, 804,
-
743 cm .
1
2
N,N-[ H10]-diethyltryptamine (5)
All reactions were initially optimized using unla-
belled compounds.
A mixture of 2-(1H-indol-3-yl)-ethylamine 4 (1.60 g,
2
0.0 mmol), [ H
1
5
]-iodoethane (5.00 g, 31.1 mmol) and an-
2
-(1H-Indol-3-yl)-ethylamine (4)
hydrous potassium carbonate (5.53 g, 40.0 mmol) in anhy-
drous methanol (10 mL) was stirred at 45-50 °C for 5 days.
After cooling to room temperature, the solid was removed
by filtration and washed with methanol. The combined fil-
trate and methanol solution was concentrated, the remained
solid was suspended in dichloromethane solution, and the
non-dissolving salt was removed by filtration. The filtrate
was concentrated, and the residue was purified by flash col-
umn chromatography using silica gel (deactivated by am-
monia) as the stationary phase and ethyl acetate-hexane
(1:9) as the mobile phase, producing a brown syrupy com-
Oxalyl chloride (17.3 mL, 198.0 mmol) was added to
a cooled and well-stirred solution of indole (20.20 g, 171.0
mmol) in anhydrous diethyl ether (340 mL). Stirring was
continued at 0 °C for an additional 3 h, and at room temper-
ature for 1 h, generating yellow solids. The yellow solids
were collected by filtration and washed with diethyl ether
to give compound 2 (33.47 g, 162.0 mmol) in a 94% yield.
A suspension solution of compound 2 (5.07 g, 24.5 mmol)
in dichloromethane (120 mL) was saturated with ammonia
gas and stirred for 30 min. The solvent was removed, and
water (240 mL) was added. The resulting aqueous solution
was extracted with ethyl acetate. The combined extracts
were washed with brine, and then dried over anhydrous
magnesium sulfate. Following filtration and concentration,
a yellowish solid of 3 (4.08 g, 21.7 mmol) was formed in an
1
pound 5 (0.45 g, 2.0 mmol). Yield: 20%. H NMR (300
MHz, CDCl
3
, d): 8.28 (s, br, 1H), 7.61( d, J = 7.1 Hz, 1H),
7.36 (d, J = 7.2 Hz, 1H), 7.20-7.07 (m, 2H), 7.07 (s, 1H),
1
3.09-3.02 (m, 2H), 2.98-2.90 (m, 2H). C NMR (75.5
3
MHz, CDCl , d): 142.5, 133.5, 128.4, 128.0, 125.3, 124.7,
3
8
9% yield. To a suspension solution of lithium aluminum
118.7, 117.7, 59.2, 52.6-51.6 (m), 28.1, 16.9-15.2 (m). IR
(KBr, thin film): 3237, 3054, 2924, 2823, 2713, 2223,
hydride (3.03 g, 79.8 mmol) in dioxane (109 mL), com-
pound 3 (1.50 g, 8.0 mmol) was added through a Soxhlet
extraction apparatus by refluxing for 34 h. Following cool-
ing in an external ice bath, the reaction complex and excess
hydride were decomposed by cautiously adding 2 M aque-
ous NaOH. The inorganic solid was removed by filtration;
the filter cake was washed using additional tetrahydro-
furan. The filtrates and washes were combined and concen-
trated to yield an aqueous solution. Diethyl ether was then
added, and the aqueous solution was acidified by 1 M hy-
drochloric acid. The aqueous solution was extracted with
diethyl ether, and the aqueous phase was basified utilizing
-
2073, 1454, 1113, 738 cm . MS-EI (m/z): 226 (M , 2), 144
1
+
+
(2.6), 130 (7.6), 96 (100), 64 (2.5). HRMS-EI (m/z): [M ]
calcd for C14
H
10
D
10
N
2
, 226.2244; found 226.2260.
2
[2-(1H-Indol-3-yl)-ethyl]-[ H
6
]-dipropylamine (DPT)
(6)
A mixture of 2-(1H-indol-3-yl)-ethylamine 4 (1.60 g,
2
10.0 mmol), 1,1,1-[ H ]-3-bromopropane (5.00 g, 39.7
3
mmol) and anhydrous potassium carbonate (5.53 g, 40.0
mmol) in anhydrous methanol (10 mL) was stirred at 55 °C
for 5 days. After cooling to room temperature, the solid was
removed by filtration and washed with methanol. The com-
bined filtrate and methanol solution was concentrated, the
remaining solid was suspended in dichloromethane solu-
tion and the non-dissolving salt was removed by filtration.
The filtrate was concentrated, and the residue was purified
2
M aqueous NaOH. The basic aqueous solution was ex-
tracted with diethyl ether, and the combined extracts were
dried over anhydrous sodium sulfate. The solvents were re-
moved in vacuo, yielding 2-(1H-indol-3-yl)-ethylamine (4)
1
0.90 g, 5.6 mmol). Yield: 70%. mp: 112-113 °C. H NMR
(

1
366 J. Chin. Chem. Soc., Vol. 54, No. 5, 2007
Wang and Chen
by flash column chromatography using silica gel (deacti-
vated by ammonia) as the stationary phase and ethyl ace-
tate-hexane (1:4) as the mobile phase, producing a brown
mixture was refluxed for 4 h. Following cooling in an ex-
ternal ice bath, the reaction complex and excess hydride
were decomposed by the cautious addition of 2 M aqueous
NaOH. The inorganic solid was removed via filtration; the
filter cake was washed using additional diethyl ether. The
filtrate and washes were combined and dried over anhy-
1
syrupy compound 6 (1.71 g, 6.8 mmol). Yield: 68%. H
NMR (300 MHz, CDCl
3
, d): 7.97 (s, br, 1H), 7.61 (d, J =
.8 Hz, 1H), 7.36 (d, J = 7.0 Hz, 1H), 7.21-7.12 (m, 2H),
.02 (s, 1H), 2.94-2.89 (m, 2H), 2.84-2.80 (m, 2H), 2.52 (t,
7
7
drous magnesium sulfate. The solvents were removed in
2
vacuo, yielding 3-(2-dimethylamino-[ H
1
3
J = 2.4 Hz, 4H), 1.51 (t, J = 7.3 Hz, 4H). C NMR (75.5
MHz, CDCl , d): 136.4, 127.7, 121.9, 121.7, 119.3, 119.1,
14.6, 111.3, 56.1, 54.9, 22.9, 20.1, 11.8-10.6 (m). IR
KBr, thin film): 3421, 3055, 2939, 2875, 2803, 2218,
4
]-ethyl)-1H-indol-
1
5-ol (8) (0.74 g, 3.85 mmol). Yield: 89%. mp: 43-44 °C. H
3
1
NMR (300 MHz, CDCl , d): 7.96 (s, 1H), 7.62 (d, J = 7.5
3
(
Hz, 1H), 7.36 (d, J = 7.9 Hz, 1H), 7.19-7.09 (m, 2H), 7.04
13
(d, J = 2.3 Hz, 1H), 2.39 (s, 6H). C NMR (100.6 MHz,
-
1
+
075, 1654, 1457, 1053, 739 cm . MS-EI (m/z): 250 (M ,
2
1
0), 164 (17), 130 (91), 120 (100), 115 (17), 103 (11), 90
3
CDCl , d): 136.8, 127.7, 122.3, 121.8, 119.1, 118.9, 113.5,
+
21), 75 (32), 46 (43). HRMS-EI (m/z): [M ] calcd for
(
111.6, 60.0-59.2 (m), 45.4, 23.1-22.7 (t). IR (thin film):
3424, 2823, 2183, 2057, 1452, 1245, 988, 796, 742, 425
16 18 6 2
C H D N , 250.2310; found 250.2312.
-
1
cm . MS-EI (m/z): 192 (M , 46), 148 (7), 132 (23), 118 (6),
+
+
104 (6), 78 (6), 60 (100). HRMS-EI (m/z): [M ] calcd for
2
-(5-Benzyloxy-1H-indol-3-yl)-N,N-dimethyl-2-oxo-
acetamide (7)
Compound 2 (1.0 g, 4.8 mmol) in a small amount of
12 12 4 2
C H D N , 192.1560; found 192.1567.
anhydrous diethyl ether was added to a solution of dimeth-
ylamine hydrochloride (13.05 g, 160.0 mmol) and sodium
hydroxide (6.37 g, 159.3 mmol) in water (15.4 mL). The
mixture was stirred for a further 30 min, and the white solid
was obtained via filtration and washed with water and di-
chloromethane. The aqueous phase was extracted with di-
chloromethane, and the combined organic phase was con-
centrated. The residue was purified by flash column chro-
matography using silica gel as the stationary phase and
methanol-ethyl acetate (1:9) as the mobile phase, produc-
3-(2-Nitro-propenyl)-1H-indole (10)
A solution of indole-3-carboxaldehyde (9) (2.17 g,
15.0 mmol) in nitroethane (8.6 mL, 119.7 mmol) was
treated with anhydrous ammonium acetate (0.39 g, 5.0
mmol) and heated at 100 °C for 2.5 h until the starting ma-
terial was completely consumed by thin layer chromatogra-
phy (TLC) monitoring. The solvent was removed under
vacuum, yielding a solid that was then washed with water.
The remaining solid was recrystallized from ethanol to give
3-(2-nitro-propenyl)-1H-indole (10) (1.90 g, 9.4 mmol) as
1
a yellow crystal. Yield: 63%. mp: 190-192 °C. H NMR
ing a brown syrupy compound 7 (0.96 g, 4.5 mmol). Yield:
1
2%. mp: 173-175 °C. H NMR (300 MHz, CDCl
9
3
, d): 9.25
(300 MHz, CDCl
3
, d): 8.70 (br, 1H), 8.52 (s, 1H), 7.83 (d, J
(
s, br, 1H), 8.37-8.38 (m, 1H), 7.93 (d, J = 4.3 Hz, 1H),
= 7.2 Hz, 1H), 7.57 (d, J = 2.8 Hz, 1H), 7.48 (d, J = 8.1 Hz,
1
3
7
1
1
.44-7.40 (m, 1H), 7.34-7.30 (m, 2H), 3.10 (s, 1H), 3.07 (s,
1H), 7.36-7.27 (m, 2H), 2.55 (s, 3H). C NMR (75.5 MHz,
CDCl , d): 142.9, 135.8, 127.6, 126.2, 124.0, 121.8, 118.9,
111.7, 110.3, 14.9. IR (KBr, thin film): 3428, 3136, 1623,
1
H). C NMR (100.6 MHz, CDCl
3
3
, d): 186.1, 168.3, 136.9,
3
36.0, 125.2, 124.1, 123.1, 121.7, 114.0, 112.3, 37.5, 34.4.
-
1527, 1471, 1420, 1268, 1223, 1103, 967, 748 cm . MS-EI
1
IR (thin film): 3103, 2925, 1630, 1523, 1447, 1245, 1127,
-
47 cm .
1
+
(m/z): 202 (M , 100), 154 (80), 145 (48), 128 (56), 117 (23),
7
+
04 (14), 77 (24), 65 (10), 51 (7). HRMS-EI (m/z): [M ]
1
2
-(2-Dimethylamino-[ H
3
4
]-ethyl)-1H-indol-5-ol (8)
calcd for C11
H
10
N
2
O
2
, 202.0742; found 202.0744.
To a well-stirred suspension of lithium aluminum
]-hydride (0.71 g, 16.9 mmol) in anhydrous tetrahydro-
2
2
2-(1H-Indol-3-yl)-1-methyl-[ H
[
H
4
2
]-ethylamine (11)
furan (20 mL), a suspension of 2-(5-benzyloxy-1H-indol-
-yl)-N,N-dimethyl-2-oxo-acetamide 7 (0.94 g, 4.35 mmol)
in tetrahydrofuran (15 mL) was added in small portions; the
A suspension of 3-(2-nitro-propenyl)-1H-indole (10)
(1.80 g, 8.9 mmol) in tetrahydrofuran (40 mL) was added in
small portions to a well-stirred suspension of lithium alu-
3

Synthesis of Deuterium Labeled Tryptamine Derivatives
J. Chin. Chem. Soc., Vol. 54, No. 5, 2007 1367
2
minum [ H
4
]-hydride (2.20 g, 53.4 mmol) in anhydrous
M. S.; Barbosa-Filho, J. M. Pharmaceut. Biol. 1999, 37, 50.
. Callaway, J. C.; McKenna, D. J.; Grob, C. S.; Brito, G. S.;
Raymon, L. P.; Poland, R. E.; Andrade, E. N.; Andrade, E.
O.; Mash, D. C. J. Ethnopharmacol. 1999, 65, 243.
6
tetrahydrofuran (40 mL); the mixture was refluxed for 2 h.
Following cooling in an external ice bath, the reaction com-
plex and excess hydride were decomposed by the cautious
addition of 2 M aqueous NaOH. The inorganic solid was re-
moved by filtration; the filter cake was washed using addi-
tional diethyl ether. The filtrate and washes were combined
and dried over anhydrous magnesium sulfate. The solvents
7
8
. Franzen, F.; Gross, H. Nature 1965, 206, 1052.
. Benington, F.; Morin, R. D.; Clark, L. C. Ala J. Med. Sci.
1
965, 2, 397.
9
. Christian, S. T.; Harrison, R.; Pagel, J. Ala J. Med. Sci. 1976,
13, 162.
were removed in vacuo, yielding 2-(1H-indol-3-yl)-1-meth-
2
yl-[ H
10. Christian, S. T.; Harrison, R.; Quayle, E.; Pagel, J.; Monti, J.
2
]-ethylamine 11 (1.46 g, 8.3 mmol). Yield: 94%.
Biochem. Med. 1977, 18, 164.
1
1
1. Barker, S. A.; Monti, J. A.; Christian, S. T. Int. Rev.
mp: 91-92 °C. H NMR (300 MHz, CDCl
3
, d): 8.14 (s, br,
H), 7.62 (d, J = 7.8 Hz, 1H), 7.37 (d, J = 7.2 Hz, 1H), 7.20-
.04 (m, 2H), 7.04 (s, 1H), 2.88 (s, 1H), 2.64 (s, 1H), 1.24
Neurobiol. 1981, 22, 83.
1
7
1
1
1
2. Barker, S. A.; Littlefield-Chabaud, M. A.; David, C. J.
Chromatogr. B 2001, 751, 37.
1
3
(
s, 3H). C NMR (75.5 MHz, CDCl
3
, d): 136.4, 127.8,
22.5, 121.8, 119.3, 119.1, 113.8, 111.2, 47.1-46.5 (t),
5.8-35.3 (t), 24.7. IR (KBr, thin film): 3415, 3357, 3299,
3. For more information, visit the following webpage at
http://en.wikipedia.org/wiki/Diethyltryptamine
4. Xu, Y. Z.; Chen, C. J. Chin.Chem. Soc. 2007, 54, 493.
1
3
2
-
863, 2129, 1573, 1455, 1353, 1005, 742, 422 cm . MS-EI
+
m/z): 176 (M , 19), 160 (1), 148 (1), 132 (100), 117 (2),
1
15. Xu, Y. Z.; Chen, C. J. Labelled Comp. Radiopharm. 2006,
49, 897.
(
+
1
04 (8), 78 (6), 46 (1). HRMS-EI (m/z): [M ] calcd for
, 176.1280; found 176.1274.
16. Xu, Y. Z.; Chen, C. J. Labelled Comp. Radiopharm. 2006,
4
9, 1187.
11 12 2 2
C H D N
1
1
1
7. Shaikh, A. C.; Wang, Y. Y.; Chen, C. J. Labelled Comp.
Radiopharm. 2007, 50, 660.
8. Balssa, F.; Bonnaire, Y. J. Labelled Comp. Radiopharm.
ACKNOWLEDGEMENTS
2
007, 50, 207.
9. Sancéau, J. Y.; Larouche, D.; Caron, B.; Bélanger, P.; Co-
quet, A.; Bélanger, A.; Labrie, F.; Gauthier, S. J. Labelled
Comp. Radiopharm. 2007, 50, 197.
The authors thank Ms. Hsu, L. M. at the Instruments
Center, National Chung Hsing University. We would also
like to thank the National Bureau of Controlled Drugs, De-
partment of Health, Taiwan, Republic of China, for finan-
cially supporting this work under Contract DOH95-NNB-
20. Hooper, J.; Watts, P. J. Labelled Comp. Radiopharm. 2007,
50, 189.
2
2
2
2
2
1. Springer, J. B.; Colvin, O. M.; Ludeman, S. M. J. Labelled
Comp. Radiopharm. 2007, 50, 115.
1
001.
2. Ismail, M. A.; David, W.; Boyki, D. W. J. Labelled Comp.
Radiopharm. 2006, 49, 985.
3. Pajk, M.; Ka½ska, M. J. Labelled Comp. Radiopharm.
Received March 29, 2007.
2
006, 49, 1061.
4. Robertson, A. A. B.; Botting, N. P. J. Labelled Comp.
Radiopharm. 2006, 49, 1201.
REFERENCES
5. Fish, M. S.; Johnson, N. M.; Horning, E. C. J. Am. Chem.
Soc. 1956, 78, 3668.
1
2
3
. Boland, D. M.; Andollo, W.; Hime, G. W.; Hearn, W. L. J.
Anal. Toxicol. 2005, 29, 394.
26. Sintas, J. A.; Vitale, A. A. J. Labelled Compd. Radiopharm.
1997, 39, 677.
. Long, H.; Nelson, L. S.; Hoffman, R. S. Vet. Hum. Toxicol.
27. Somei, M.; Kobayashi, K.; Tanii, K.; Mochizuki, T.;
Kawada, Y.; Fukui, Y. Heterocycles 1995, 40, 119.
28. Chen, C. Y.; Senanayake, C. H.; Bill, T. J.; Larsen, R. D.;
Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1994, 59, 3738.
29. Tymiak, A. A.; Rinehart, K. L.; Bakus, G. J. Tetrahedron
1985, 41, 1039.
2
003, 45, 149.
. McKenna, D. J.; Towers, G. H.; Abbott, F. J. Ethnophar-
macol. 1984, 10, 195.
4
. Ott, J. J. Psychoact. Drugs 1999, 31, 171.
. Batista, L. M.; Almeida, R. N.; da-Chuna, E. V. L.; da-Silva,
5

1
368 J. Chin. Chem. Soc., Vol. 54, No. 5, 2007
Wang and Chen
3
0. Wu, T. Y. H.; Schultz, P. G. Org. Lett. 2002, 4, 4033.
1. For more information, visit the following webpage at
http://www.erowid.org/chemicals/dmt/dmt_synthesis1.
shtml
Thompson, C. M.; Parker, K. K. Pharmacology 2005, 74,
193.
3
33. Young, E. H. P. J. Chem. Soc. 1958, 3493.
34. Lloyd, D. H.; Nicholas, D. E. J. Org.Chem. 1986, 51, 4294.
3
2. Thiagaraj, H. V.; Russo, E. B.; Burnett, A.; Goldstein, E.;