SDB-005

Last updated
SDB-005
SDB-005 structure.png
Legal status
Legal status
Identifiers
  • Naphthalen-1-yl 1-pentyl-1H-indazole-3-carboxylate
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
Formula C23H22N2O2
Molar mass 358.441 g·mol−1
3D model (JSmol)
  • CCCCCN1N=C(C(=O)OC2=CC=CC3=C2C=CC=C3)C2=C1C=CC=C2
  • InChI=1S/C23H22N2O2/c1-2-3-8-16-25-20-14-7-6-13-19(20)22(24-25)23(26)27-21-15-9-11-17-10-4-5-12-18(17)21/h4-7,9-15H,2-3,8,16H2,1H3
  • Key:JBVNFKZVDLFOAY-UHFFFAOYSA-N

SDB-005 is an indazole-based synthetic cannabinoid that has been sold online as a designer drug. [1] It is presumed to be an agonist of the CB1 and CB2 cannabinoid receptors. SDB-005 is the indazole core analog of PB-22 where the 8-hydroxyquinoline has also been replaced with a naphthalene group.

The code number SDB-005 was originally used for a different compound, the N-phenyl instead of N-benzyl analogue of SDB-006. This compound is a potent agonist of the CB1 receptor (Ki = 21 nM) and CB2 receptor (Ki = 140 nM). [2]

Original, non designer drug SDB-005 OriginalSDB005 structure.png
Original, non designer drug SDB-005

However, SDB-005 was subsequently used as the name for the indazole-3-carboxylate compound mentioned above when it was sold in Europe as a designer drug, and was entered into the EMCDDA synthetic drug database under this name. [3] Consequently, there are now two distinct, yet fairly closely related cannabinoid compounds, which may both be referred to under the code SDB-005.

See also

Related Research Articles

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MN 18 is an indazole-based synthetic cannabinoid that is an agonist for the cannabinoid receptors, with Ki values of 45.72 nM at CB1 and 11.098 nM at CB2 and EC50 values of 2.028 nM at CB1 and 1.233 nM at CB2, and has been sold online as a designer drug. It is the indazole core analogue of NNE1. Given the known metabolic liberation (and presence as an impurity) of amantadine in the related compound APINACA, it is suspected that metabolic hydrolysis of the amide group of MN-18 may release 1-naphthylamine, a known carcinogen. MN-18 metabolism has been described in literature.

<span class="mw-page-title-main">JWH-018</span> Chemical compound

JWH-018 (1-pentyl-3-(1-naphthoyl)indole) or AM-678 is an analgesic chemical from the naphthoylindole family that acts as a full agonist at both the CB1 and CB2 cannabinoid receptors, with some selectivity for CB2. It produces effects in animals similar to those of tetrahydrocannabinol (THC), a cannabinoid naturally present in cannabis, leading to its use in synthetic cannabis products that in some countries are sold legally as "incense blends".

<span class="mw-page-title-main">AM-2201</span> Chemical compound

AM-2201 is a recreational designer drug that acts as a potent but nonselective full agonist for the cannabinoid receptor. It is part of the AM series of cannabinoids discovered by Alexandros Makriyannis at Northeastern University.

<span class="mw-page-title-main">MDA-19</span> Chemical compound

MDA-19 (also known as BZO-HEXOXIZID) is a drug that acts as a potent and selective agonist for the cannabinoid receptor CB2, with reasonable selectivity over the psychoactive CB1 receptor, though with some variation between species. In animal studies it was effective for the treatment of neuropathic pain, but did not effect rat locomotor activity in that specific study. The pharmacology of MDA-19 in rat cannabinoid receptors have been demonstrated to function differently than human cannabinoid receptors with MDA-19 binding to human CB1 receptors 6.9x higher than rat CB1 receptors.

UR-144 Chemical compound

UR-144 (TMCP-018, KM-X1, MN-001, YX-17) is a drug invented by Abbott Laboratories, that acts as a selective full agonist of the peripheral cannabinoid receptor CB2, but with much lower affinity for the psychoactive CB1 receptor.

APICA (synthetic cannabinoid drug) Chemical compound

APICA is an indole based drug that acts as a potent agonist for the cannabinoid receptors.

<span class="mw-page-title-main">STS-135 (drug)</span> Chemical compound

STS-135 (N-(adamantan-1-yl)-1-(5-fluoropentyl)-1H-indole-3-carboxamide, also called 5F-APICA) is a designer drug offered by online vendors as a cannabimimetic agent. The structure of STS-135 appears to use an understanding of structure-activity relationships within the indole class of cannabimimetics, although its design origins are unclear. STS-135 is the terminally-fluorinated analogue of SDB-001, just as AM-2201 is the terminally-fluorinated analogue of JWH-018, and XLR-11 is the terminally-fluorinated analogue of UR-144. STS-135 acts a potent cannabinoid receptor agonist in vitro, with an EC50 of 51 nM for human CB2 receptors, and 13 nM for human CB1 receptors. STS-135 produces bradycardia and hypothermia in rats at doses of 1–10 mg/kg, suggesting cannabinoid-like activity.

PB-22 Chemical compound

PB-22 is a designer drug offered by online vendors as a cannabimimetic agent, and detected being sold in synthetic cannabis products in Japan in 2013. PB-22 represents a structurally unique synthetic cannabinoid chemotype, since it contains an ester linker at the indole 3-position, rather than the precedented ketone of JWH-018 and its analogs, or the amide of APICA and its analogs.

QUCHIC Chemical compound

QUCHIC is a designer drug offered by online vendors as a cannabimimetic agent, and was first detected being sold in synthetic cannabis products in Japan in early 2013, and subsequently also in New Zealand. The structure of QUCHIC appears to use an understanding of structure-activity relationships within the indole class of cannabimimetics, although its design origins are unclear. QUCHIC, along with QUPIC, represents a structurally unique synthetic cannabinoid chemotype since it contains an ester linker at the indole 3-position rather than the precedented ketone of JWH-018 and its analogues, or the amide of SDB-001 and its analogues.

5F-PB-22 Chemical compound

5F-PB-22 is a designer drug which acts as a cannabinoid agonist. The structure of 5F-PB-22 appears to have been designed with an understanding of structure–activity relationships within the indole class of cannabinoids.

<span class="mw-page-title-main">SDB-006</span> Chemical compound

SDB-006 is a drug that acts as a potent agonist for the cannabinoid receptors, with an EC50 of 19 nM for human CB2 receptors, and 134 nM for human CB1 receptors. It was discovered during research into the related compound SDB-001 which had been sold illicitly as "2NE1". SDB-006 metabolism has been described in literature.

THJ-2201 Synthetic cannabinoid

THJ-2201 is an indazole-based synthetic cannabinoid that presumably acts as a potent agonist of the CB1 receptor and has been sold online as a designer drug.

5F-SDB-006 Chemical compound

5F-SDB-006 is a drug that acts as a potent agonist for the cannabinoid receptors, with an EC50 of 50 nM for human CB1 receptors, and 123 nM for human CB2 receptors. It was discovered during research into the related compound APICA which had been sold illicitly as "2NE1". 5F-SDB-006 is the terminally fluorinated analog of SDB-006, just as STS-135 is the terminally fluorinated analog of APICA. Given the known metabolic liberation (and presence as an impurity) of amantadine in the related compound APINACA, it is suspected that metabolic hydrolysis of the amide group of 5F-SDB-006 may release benzylamine.

<span class="mw-page-title-main">NNE1</span>

NNE1 (also known as NNEI, MN-24 and AM-6527) is an indole-based synthetic cannabinoid, representing a molecular hybrid of APICA and JWH-018 that is an agonist for the cannabinoid receptors, with Ki values of 60.09 nM at CB1 and 45.298 nM at CB2 and EC50 values of 9.481 nM at CB1 and 1.008 nM at CB2. It was invented by Abbott and has a CB1 receptor pEC50 of 8.9 with around 80x selectivity over the related CB2 receptor. It is suspected that metabolic hydrolysis of the amide group of NNE1 may release 1-naphthylamine, a known carcinogen, given the known metabolic liberation (and presence as an impurity) of amantadine in the related compound APINACA, and NNE1 was banned in New Zealand in 2012 as a temporary class drug to stop it being used as an ingredient in then-legal synthetic cannabis products. NNE1 was subsequently found to be responsible for the death of a man in Japan in 2014.

THJ-018 Chemical compound

THJ-018 (SGT-17) is a synthetic cannabinoid that is the indazole analogue of JWH-018 and has been sold online as a designer drug.

NM-2201 Chemical compound

NM-2201 (also known as CBL-2201) is an indole-based synthetic cannabinoid that presumably has similar properties to the closely related 5F-PB-22 and NNE1, which are both full agonists and unselectively bind to CB1 and CB2 receptors with low nanomolar affinity.

<span class="mw-page-title-main">5F-PCN</span>

5F-PCN (also known as 5F-MN-21) is an azaindole-based synthetic cannabinoid that is presumed to be a potent agonist of the CB1 receptor and has been sold online as a designer drug. It is closely related to NNE1. Given the known metabolic liberation (and presence as an impurity) of amantadine in the related compound APINACA, it is suspected that metabolic hydrolysis of the amide group of 5F-PCN may release 1-naphthylamine, a known carcinogen.

QMPSB Chemical compound

QMPSB is an arylsulfonamide-based synthetic cannabinoid that has been sold as a designer drug.

<span class="mw-page-title-main">CUMYL-FUBINACA</span> Chemical compound

CUMYL-FUBINACA (SGT-149) is an indazole-3-carboxamide based synthetic cannabinoid receptor agonist, with an EC50 of 1.8nM for human CB1 receptors and 23.7nM for human CB2 receptors, giving it around 13x selectivity for CB1. It has been sold online as a designer drug.

References

  1. "SDB-005". Cayman Chemical. Retrieved 27 June 2015.
  2. Banister SD, Wilkinson SM, Longworth M, Stuart J, Apetz N, English K, et al. (July 2013). "The synthesis and pharmacological evaluation of adamantane-derived indoles: cannabimimetic drugs of abuse". ACS Chemical Neuroscience. 4 (7): 1081–92. doi:10.1021/cn400035r. PMC   3715837 . PMID   23551277.
  3. EWS_EU: Neue Psychoaktive Substanzen, April 2015