diff --git a/crates/codegen/src/compile.rs b/crates/codegen/src/compile.rs
index 6f7d8c152..b4e24a304 100644
--- a/crates/codegen/src/compile.rs
+++ b/crates/codegen/src/compile.rs
@@ -9069,6 +9069,18 @@ mod tests {
 
     fn compile_exec(source: &str) -> CodeObject {
         let opts = CompileOpts::default();
+        compile_exec_with_options(source, opts)
+    }
+
+    fn compile_exec_optimized(source: &str) -> CodeObject {
+        let opts = CompileOpts {
+            optimize: 1,
+            ..CompileOpts::default()
+        };
+        compile_exec_with_options(source, opts)
+    }
+
+    fn compile_exec_with_options(source: &str, opts: CompileOpts) -> CodeObject {
         let source_file = SourceFileBuilder::new("source_path", source).finish();
         let parsed = ruff_python_parser::parse(
             source_file.source_text(),
@@ -9137,6 +9149,15 @@ x = Test() and False or False
         ));
     }
 
+    #[test]
+    fn test_const_bool_not_op() {
+        assert_dis_snapshot!(compile_exec_optimized(
+            "\
+x = not True
+"
+        ));
+    }
+
     #[test]
     fn test_nested_double_async_with() {
         assert_dis_snapshot!(compile_exec(
diff --git a/crates/codegen/src/ir.rs b/crates/codegen/src/ir.rs
index 43a2dfa51..52499664f 100644
--- a/crates/codegen/src/ir.rs
+++ b/crates/codegen/src/ir.rs
@@ -693,6 +693,33 @@ impl CodeInfo {
                                 None
                             }
                         }
+                        (Instruction::LoadConst { consti }, Instruction::ToBool) => {
+                            let consti = consti.get(curr.arg);
+                            let constant = &self.metadata.consts[consti as usize];
+                            if let ConstantData::Boolean { .. } = constant {
+                                Some((curr_instr, OpArg::from(consti)))
+                            } else {
+                                None
+                            }
+                        }
+                        (Instruction::LoadConst { consti }, Instruction::UnaryNot) => {
+                            let constant = &self.metadata.consts[consti.get(curr.arg) as usize];
+                            match constant {
+                                ConstantData::Boolean { value } => {
+                                    let (const_idx, _) = self
+                                        .metadata
+                                        .consts
+                                        .insert_full(ConstantData::Boolean { value: !value });
+                                    Some((
+                                        (Instruction::LoadConst {
+                                            consti: Arg::marker(),
+                                        }),
+                                        OpArg::new(const_idx as u32),
+                                    ))
+                                }
+                                _ => None,
+                            }
+                        }
                         _ => None,
                     }
                 };
diff --git a/crates/codegen/src/snapshots/rustpython_codegen__compile__tests__const_bool_not_op.snap b/crates/codegen/src/snapshots/rustpython_codegen__compile__tests__const_bool_not_op.snap
new file mode 100644
index 000000000..f9a74c205
--- /dev/null
+++ b/crates/codegen/src/snapshots/rustpython_codegen__compile__tests__const_bool_not_op.snap
@@ -0,0 +1,9 @@
+---
+source: crates/codegen/src/compile.rs
+expression: "compile_exec_optimized(\"\\\nx = not True\n\")"
+---
+  1           0 RESUME               (0)
+              1 LOAD_CONST           (False)
+              2 STORE_NAME           (0, x)
+              3 LOAD_CONST           (None)
+              4 RETURN_VALUE