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Ketamine

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Ketamine

Ketamine is a cyclohexanone-derived general anesthetic and NMDA receptor antagonist with analgesic and hallucinogenic properties, used medically for anesthesia, depression, and pain management. Ketamine exists as its two enantiomers, S- (esketamine) and R- (arketamine), and has antidepressant action likely involving other mechanisms in addition to NMDA antagonism. At anesthetic doses, ketamine induces a state of dissociative anesthesia, a trance-like state providing pain relief, sedation, and amnesia. Its distinguishing features as an anesthestic are preserved breathing and airway reflexes, stimulated heart function with increased blood pressure, and moderate bronchodilation. As an anesthetic, it is used especially in trauma, emergency, and pediatric cases. At lower, sub-anesthetic doses, it is used as a treatment for pain and treatment-resistant depression. Ketamine is legally used in medicine but is also tightly controlled, as it is used as a recreational drug for its hallucinogenic and dissociative effects. When used recreationally, it is found both in crystalline powder and liquid form, and is often referred to by users as "Ket", "Special K" or simply "K". The long-term effects of repeated use are largely unknown and are an area of active investigation. Liver and urinary toxicity have been reported among regular users of high doses of ketamine for recreational purposes. Ketamine can cause dissociation and nausea, and other adverse effects, and is contraindicated in severe heart or liver disease, and uncontrolled psychosis. Ketamine’s clinical and antidepressant effects can be influenced by co-administration of other drugs, though these interactions are variable and not yet fully understood. Ketamine was first synthesized in 1962; it was derived from phencyclidine in pursuit of a safer anesthetic with fewer hallucinogenic effects. It was approved for use in the United States in 1970. It has been regularly used in veterinary medicine and was extensively used for surgical anesthesia in the Vietnam War. It later gained prominence for its rapid antidepressant effects discovered in 2000, marking a major breakthrough in depression treatment. Racemic ketamine, especially at higher doses, may be more effective and longer-lasting than esketamine in reducing depression severity. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication.

Infobox

Trade names
Ketalar, others
Other names
CI-581; CL-369; CM-52372-2
AHFS/Drugs.com
Monograph
License data
mw- US DailyMed: Ketamine
Pregnancycategory
AU: B3
Addictionliability
Moderate–high
Routes ofadministration
Any
Drug class
NMDA receptor antagonist; general anesthetic; dissociative hallucinogen; analgesic; antidepressant
ATC code
N01AX03 (WHO)
Legal status
AU: S8 (Controlled drug) BR: Class C1 (Other controlled substances) CA: Schedule I DE: § 48 AMG/§ 1 MPAV (Prescription only) UK: Class B (Class A if prepared as an injection) US: Schedule III UN: Unscheduled (Rx only) IN: Schedule X
Bioavailability
Intravenous: 100% Intramuscular: 93% Epidural: 77% Intranasal: 45–50% Sublingual: 24–30% Rectal: 25–30% By mouth: 16–20%
Protein binding
23–47%
Metabolism
Liver, intestine (oral): Major: CYP3A4, CYP2B6
Metabolites
Norketamine Dehydronorketamine Hydroxynorketamine
Onset of action
Intravenous: seconds Intramuscular: 1–5 min Subcutaneous: 15–30 min Insufflation: 5–10 min By mouth: 15–30 min
Elimination half-life
Ketamine: 2.5–3 hours Norketamine: 12 hours
Duration of action
Intramuscular: 0.5–2 hours Insufflation: 45–60 min By mouth: 1–6 hours
Excretion
Urine: 91% Feces: 3%
CAS Number
6740-88-1 Y 33643-46-8 (esketamine) 33643-49-1 (arketamine) HCl: 1867-66-9 Y
PubChem CID
3821
IUPHAR/BPS
4233
DrugBank
DB01221 Y
ChemSpider
3689 Y
UNII
690G0D6V8H
KEGG
D08098 YHCl: D00711 Y
ChEBI
CHEBI:6121 Y
ChEMBL
ChEMBL742 Y
CompTox Dashboard (EPA)
DTXSID8023187
ECHA InfoCard
100.027.095
Formula
C13H16ClNO
Molar mass
237.73 g·mol−1
3D model (JSmol)
Interactive image
Chirality
Racemic mixture: Esketamine (S( )-isomer) Arketamine (R(−)-isomer)
Melting point
92 °C (198 °F)

Tables

Ketamine and biological targets (with Ki below 100 μM) · Pharmacology › Pharmacodynamics › Molecular targets
NMDATooltip N-Methyl-D-aspartate receptor
NMDATooltip N-Methyl-D-aspartate receptor
Site
NMDATooltip N-Methyl-D-aspartate receptor
Value (μM)
0.25–0.66
Type
Ki
Action
Antagonist
Species
Human
MORTooltip μ-Opioid receptor
MORTooltip μ-Opioid receptor
Site
MORTooltip μ-Opioid receptor
Value (μM)
42
Type
Ki
Action
Antagonist
Species
Human
MOR2Tooltip μ-Opioid receptor
MOR2Tooltip μ-Opioid receptor
Site
MOR2Tooltip μ-Opioid receptor
Value (μM)
12.1
Type
Ki
Action
Antagonist
Species
Human
KORTooltip κ-Opioid receptor
KORTooltip κ-Opioid receptor
Site
KORTooltip κ-Opioid receptor
Value (μM)
2825
Type
KiKi
Action
AntagonistAgonist
Species
Human
σ2
σ2
Site
σ2
Value (μM)
26
Type
Ki
Action
ND
Species
Rat
D2
D2
Site
D2
Value (μM)
0.5>10
Type
KiKi
Action
AgonistND
Species
Human
M1
M1
Site
M1
Value (μM)
45
Type
Ki
Action
ND
Species
Human
α2β2Tooltip Nicotinic acetylcholine receptor
α2β2Tooltip Nicotinic acetylcholine receptor
Site
α2β2Tooltip Nicotinic acetylcholine receptor
Value (μM)
92
Type
IC50
Action
Antagonist
Species
Human
α2β4Tooltip Nicotinic acetylcholine receptor
α2β4Tooltip Nicotinic acetylcholine receptor
Site
α2β4Tooltip Nicotinic acetylcholine receptor
Value (μM)
29
Type
IC50
Action
Antagonist
Species
Human
α3β2
α3β2
Site
α3β2
Value (μM)
50
Type
IC50
Action
Antagonist
Species
Human
α3β4
α3β4
Site
α3β4
Value (μM)
9.5
Type
IC50
Action
Antagonist
Species
Human
α4β2
α4β2
Site
α4β2
Value (μM)
72
Type
IC50
Action
Antagonist
Species
Human
α4β4
α4β4
Site
α4β4
Value (μM)
18
Type
IC50
Action
Antagonist
Species
Human
α7
α7
Site
α7
Value (μM)
3.1 (HNK)
Type
IC50
Action
NAM
Species
Rat
ERαTooltip Estrogen receptor alpha
ERαTooltip Estrogen receptor alpha
Site
ERαTooltip Estrogen receptor alpha
Value (μM)
0.34
Type
Ki
Action
ND
Species
Human
NETTooltip Norepinephrine transporter
NETTooltip Norepinephrine transporter
Site
NETTooltip Norepinephrine transporter
Value (μM)
82–291
Type
IC50
Action
Inhibitor
Species
Human
DATTooltip Dopamine transporter
DATTooltip Dopamine transporter
Site
DATTooltip Dopamine transporter
Value (μM)
63
Type
Ki
Action
Inhibitor
Species
Rat
HCN1Tooltip Hyperpolarization-activated cyclic nucleotide-gated channel 1
HCN1Tooltip Hyperpolarization-activated cyclic nucleotide-gated channel 1
Site
HCN1Tooltip Hyperpolarization-activated cyclic nucleotide-gated channel 1
Value (μM)
8–16
Type
EC50
Action
Inhibitor
Species
Mouse
TRPV1
TRPV1
Site
TRPV1
Value (μM)
1-100
Type
Ki
Action
Agonist
Species
Rat
The smaller the value, the stronger the interaction with the site.
The smaller the value, the stronger the interaction with the site.
Site
The smaller the value, the stronger the interaction with the site.
Site
Value (μM)
Type
Action
Species
Ref
NMDATooltip N-Methyl-D-aspartate receptor
0.25–0.66
Ki
Antagonist
Human
MORTooltip μ-Opioid receptor
42
Ki
Antagonist
Human
MOR2Tooltip μ-Opioid receptor
12.1
Ki
Antagonist
Human
KORTooltip κ-Opioid receptor
2825
KiKi
AntagonistAgonist
Human
σ2
26
Ki
ND
Rat
D2
0.5>10
KiKi
AgonistND
Human
M1
45
Ki
ND
Human
α2β2Tooltip Nicotinic acetylcholine receptor
92
IC50
Antagonist
Human
α2β4Tooltip Nicotinic acetylcholine receptor
29
IC50
Antagonist
Human
α3β2
50
IC50
Antagonist
Human
α3β4
9.5
IC50
Antagonist
Human
α4β2
72
IC50
Antagonist
Human
α4β4
18
IC50
Antagonist
Human
α7
HNK)
IC50
NAM
Rat
ERαTooltip Estrogen receptor alpha
0.34
Ki
ND
Human
NETTooltip Norepinephrine transporter
82–291
IC50
Inhibitor
Human
DATTooltip Dopamine transporter
63
Ki
Inhibitor
Rat
HCN1Tooltip Hyperpolarization-activated cyclic nucleotide-gated channel 1
8–16
EC50
Inhibitor
Mouse
TRPV1
1-100
Ki
Agonist
Rat
The smaller the value, the stronger the interaction with the site.

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